2-methyl-1-benzofuran-4-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirred mixture of 4-hydroxy-2-methylbenzofuran (7.1 g, 0.048 M), anhydrous powdered potassium carbonate (19.87 g) and acetone (82 ml), was added dropwise bromomethoxymethane (11.99 g, 7.88 ml, 0.0959 M) with ice cooling. After the addition was complete the reaction mixture was stirred at room temperature overnight, filtered and evaporated. The residual oil was distilled to give 4-methoxymethoxy-2-methylbenzofuran, b.p. 94°-97° C./0.8 mmHg. After the addition filtered evaporated The residual oil was distilled

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

Procedure: 4-Hydroxy-2-methylbenzofuran (7.4 g, 0.05 M), ethyl 4-bromomethylbenzoate (12.15 g, 0.05 M), anhydrous potassium carbonate (7.59 g), sodium iodide (0.3 g), and 95% ethanol were reacted together in an analogous manner to that described in example 5(A) to give ethyl 4-(2-methyl-4-benzofuranyloxymethyl)benzoate which was recrystallised from ethanol/water, m.p. 59°-61° C. (Found: C, 73.73; H, 6.03. C19H18O4 requires C, 73.55; H, 5.81%).

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

Procedure: 4-Hydroxy-2-methylbenzofuran (7.4 g, 0.05 M), ethyl 4-bromomethylbenzoate (12.15 g, 0.05 M), anhydrous potassium carbonate (7.59 g), sodium iodide (0.3 g), and 95% ethanol were reacted together in an analogous manner to that described in example 5(A) to give ethyl 4-(2-methyl-4-benzofuranyloxymethyl)benzoate which was recrystallised from ethanol/water, m.p. 59°-61° C. (Found: C, 73.73; H, 6.03. C19H18O4 requires C, 73.55; H, 5.81%).

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

Procedure: 4-Hydroxy-2-methylbenzofuran (5.18 g, 0.035 M), 4-bromomethylbenzonitrile (6.86 g, 0.035 M), anhydrous potassium carbonate (5.2 g), sodium iodide (0.21 g) and 95% ethanol (50 ml) were reacted together in an analogous manner to that described in Example 5(A) to give 4-(2-methyl-4-benzofuranyloxymethyl)benzonitrile, m.p. 84°-85° C. (Found: C, 77.57; H, 5.02; N, 5.22. C17H13NO2 requires C, 77.55; H, 4.98; N, 5.32%).

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

Procedure: 4-Hydroxy-2-methylbenzofuran (5.18 g, 0.035 M), 4-bromomethylbenzonitrile (6.86 g, 0.035 M), anhydrous potassium carbonate (5.2 g), sodium iodide (0.21 g) and 95% ethanol (50 ml) were reacted together in an analogous manner to that described in Example 5(A) to give 4-(2-methyl-4-benzofuranyloxymethyl)benzonitrile, m.p. 84°-85° C. (Found: C, 77.57; H, 5.02; N, 5.22. C17H13NO2 requires C, 77.55; H, 4.98; N, 5.32%).

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

Procedure: 4-Hydroxy-2-methylbenzofuran (2/3 g, 14.4 M), methyl 2-bromomethylbenzoate (3.29 g, 14.4 mM), anhydrous potassium carbonate (2.135 g), sodium iodide (87 mg) and methanol (20 ml) were reacted together in an analogous manner to that described in Example 5(A) to give methyl 2-(2-methyl-4-benzofuranyloxymethyl)benzoate, m.p. 93°-95° C. (Found: C, 72.74; H, 5.26. C18H16O4 required C, 72.96; H, 5.44%).

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

Procedure: 4-Hydroxy-2-methylbenzofuran (2/3 g, 14.4 M), methyl 2-bromomethylbenzoate (3.29 g, 14.4 mM), anhydrous potassium carbonate (2.135 g), sodium iodide (87 mg) and methanol (20 ml) were reacted together in an analogous manner to that described in Example 5(A) to give methyl 2-(2-methyl-4-benzofuranyloxymethyl)benzoate, m.p. 93°-95° C. (Found: C, 72.74; H, 5.26. C18H16O4 required C, 72.96; H, 5.44%).

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Following the procedure of Example 32, and reacting epichlorohydrin with 4-hydroxy-2-methylbenzofuran, 4-hydroxybenzofuran, 5-hydroxybenzofuran, 5-hydroxy-2-methylbenzofuran, 6-hydroxy-3-methylbenzofuran or 7-hydroxybenzofuran, in the presence of piperidine, dissolving the thus obtained raw epoxide in absolute ethanol and adding thereto an ethanol solution of 2-aminotetralin, the following compounds are obtained respectively adding

Conditions: temp:0.00; pressure:0.00; stir: