(E)-hexadec-2-enal

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

Procedure: To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt. 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2CH2CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes): trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+). the mixture was filtered (through Celite diatomaceous earth) The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid Distillation (90-100° C./0.40-0.45 torr)

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

Procedure: To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt. 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2CH2CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes): trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+). the mixture was filtered (through Celite diatomaceous earth) The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid Distillation (90-100° C./0.40-0.45 torr)

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

Procedure: To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90°-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt, 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2, CH 2 CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes):trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+). the mixture was filtered (through Celite diatomaceous earth) The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid Distillation (90°-100° C./0.40-0.45 torr)

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

Procedure: To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90°-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt, 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2, CH 2 CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes):trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+). the mixture was filtered (through Celite diatomaceous earth) The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid Distillation (90°-100° C./0.40-0.45 torr)

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

Procedure: RF =0.5, petroleum ether (boiling point 35°-80° C./ethyl acetate 9:1; UV: blue coloration with anisaldehyde reagent (0.5 ml anisaldehyde, 50 ml glacial acetic acid, 1 ml H2SO4); boiling point (10-3Torr): 115° C. 115° C.

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

Procedure: To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt. 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2CH2CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes): trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+). the mixture was filtered (through Celite diatomaceous earth) The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid Distillation (90-100° C./0.40-0.45 torr)

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

Procedure: To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90°-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt, 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2, CH 2 CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes):trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+). the mixture was filtered (through Celite diatomaceous earth) The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid Distillation (90°-100° C./0.40-0.45 torr)