N-[[4-(hydroxymethyl)phenyl]methyl]acetamide

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

Procedure: To a solution of N-(4-hydroxymethylphenylmethyl)acetamide (1.5 g) in chloroform (50 ml) was added thionyl chloride (0.73 ml) and the mixture was refluxed under heating for 1 hr. The solvent was evaporated and the obtained residue was crystallized from ethyl acetate to give the objective N-(4-chloromethylphenylmethyl)acetamide (1.8 g) as pale-yellow crystals, melting point 116-118° C. the mixture was refluxed under heating for 1 hr The solvent was evaporated the obtained residue was crystallized from ethyl acetate

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

Procedure: To a suspension of lithium aluminum hydride (570 mg) in THF (80 ml) was added a solution of methyl 4-acetamidomethylbenzoate (3.1 g) in THF (20 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 1.5 hr. A saturated aqueous sodium sulfate solution (7 ml) was added at 10° C., and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration and the solvent was evaporated to give the objective N-(4-hydroxymethylphenylmethyl)acetamide (2.8 g) as a white solid. cooling the mixture was stirred at room temperature for 1 hr The precipitate was collected by filtration the solvent was evaporated

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

Procedure: To a solution of N-(4-hydroxymethylphenylmethyl)acetamide (1.5 g) in chloroform (50 ml) was added thionyl chloride (0.73 ml) and the mixture was refluxed under heating for 1 hr. The solvent was evaporated and the obtained residue was crystallized from ethyl acetate to give the title compound (1.8 g) as pale-yellow crystals. the mixture was refluxed under heating for 1 hr The solvent was evaporated the obtained residue was crystallized from ethyl acetate

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

Procedure: To a suspension of aluminum lithium hydride (570 mg) in tetrahydrofuran (80 ml) was added a solution of methyl 4-acetamidomethylbenzoate (3.1 g) in tetrahydrofuran (20 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 1.5 hr. A saturated aqueous sodium sulfate solution (7 ml) was added at 10° C., and the mixture was stirred at room temperature for 1 hr. The sediment was filtered off and the solvent was evaporated to give the title compound (2.8 g) as a white solid. cooling the mixture was stirred at room temperature for 1 hr The sediment was filtered off the solvent was evaporated

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

Procedure: To a solution of N-(4-hydroxymethylphenylmethyl)acetamide (1.5 g) in chloroform (50 ml) was added thionyl chloride (0.73 ml) and the mixture was refluxed under heating for 1 hr. The solvent was evaporated and the obtained residue was crystallized from ethyl acetate to give the title compound (1.8 g) as pale-yellow crystals. the mixture was refluxed under heating for 1 hr The solvent was evaporated the obtained residue was crystallized from ethyl acetate

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

Procedure: To a suspension of aluminum lithium hydride (570 mg) in tetrahydrofuran (80 ml) was added a solution of methyl 4-acetamidomethylbenzoate (3.1 g) in tetrahydrofuran (20 ml) under ice-cooling. The mixture was stirred at room temperature for 1.5 hr and a saturated aqueous sodium sulfate solution (7 ml) was added at 100° C. The mixture was stirred at room temperature for 1 hr. The sediment was filtrated and the solvent was evaporated to give the title substance (2.8 g) as a white solid. cooling The mixture was stirred at room temperature for 1 hr The sediment was filtrated the solvent was evaporated to give the title substance (2.8 g) as a white solid