4-chloro-3-methylbenzaldehyde

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol. Wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol.wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the method described for preparing compound 7.1, using compound 21.3 and 4-chloro-3-methylbenzaldehyde as the starting materials. 1H NMR (400 MHz) (CDCl3) δ 9.86 (1H, s); 7.62 (1H, s); 7.44 (1H, d, J=8.1 Hz); 7.33(1H, s); 6.70 (1H, s); 6.62 (1H, d, J=8.1 Hz);4.68 (2H, s); 4.29 (2H, q, J=7.1 Hz); 2.46 (3H, s); 2.29 (3H, s); 2.26 (3H, s); 1.32 (3H, t, J=7.1 Hz).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the method described for preparing compound 7.1, using compound 21.3 and 4-chloro-3-methylbenzaldehyde as the starting materials. 1H NMR (400 MHz) (CDCl3) δ 9.86 (1H, s); 7.62 (1H, s); 7.44 (1H, d, J=8.1 Hz); 7.33(1H, s); 6.70 (1H, s); 6.62 (1H, d, J=8.1 Hz);4.68 (2H, s); 4.29 (2H, q, J=7.1 Hz); 2.46 (3H, s); 2.29 (3H, s); 2.26 (3H, s); 1.32 (3H, t, J=7.1 Hz).

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol. Wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol.wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol.wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the method described for preparing compound 7.1, using compound 21.3 and 4-chloro-3-methylbenzaldehyde as the starting materials. 1H NMR (400 MHz) (CDCl3) δ 9.86 (1H, s); 7.62 (1H, s); 7.44 (1H, d, J=8.1 Hz); 7.33 (1H, s); 6.70 (1H, s); 6.62 (1H, d, J=8.1 Hz); 4.68 (2H, s); 4.29 (2H, q, J=7.1 Hz); 2.46 (3H, s); 2.29 (3H, s); 2.26 (3H, s); 1.32 (3H, t, J=7.1 Hz).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the method described for preparing compound 7.1, using compound 21.3 and 4-chloro-3-methylbenzaldehyde as the starting materials. 1H NMR (400 MHz) (CDCl3) δ 9.86 (1H, s); 7.62 (1H, s); 7.44 (1H, d, J=8.1 Hz); 7.33(1H, s); 6.70 (1H, s); 6.62 (1H, d, J=8.1 Hz);4.68 (2H, s); 4.29 (2H, q, J=7.1 Hz); 2.46 (3H, s); 2.29 (3H, s); 2.26 (3H, s); 1.32 (3H, t, J=7.1 Hz).

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol. Wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 216.00 g of aluminum chloride (mol. Wt. 133.34; 1,619.9 mmol), 109.09 g (4-Methylanisole (mol. Wt. 122.17; 892.9 mmol), and about 522.35 g of 2-chlorotoluene (mol. Wt. 126.59; 4,126.3 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 30° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 550 psi, the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene, and left about 76.01 g of a benzaldehyde mixture consisting of 4-chloro-3-methylbenzaldehyde (76.5%) and 3-chloro-4-methylbenzaldehyde (23.5%) (mol.wt. 154.59; 491.7 mmol; yield of approximately 67.6%). The vessel was sealed purged three times with carbon monoxide with the pressure of the vessel increased to 100 psi for each purging After the third purge the pressure at which the reaction was maintained for the total reaction time of about 66 hours (the reaction temperature was maintained at 30° C. for the duration as well) was poured into about 500 mL of ice water (which was added 500 mL of cyclohexane The top, organic layer was removed washed three times with water using a separatory funnel dried over magnesium sulfate The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 2-chlorotoluene left about 76.01 g of a benzaldehyde mixture