4-(hydroxymethyl)-2-methylphenol

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

Procedure: To a solution of 4-(hydroxymethyl)-2-methylphenol (7.95 g, 57 mmol) in dry acetonitrile (300 mL) at 5° C., was added cesium carbonate (20.42 g, 62 mmol) and ethyl bromoacetate (6.38 mL, 57 mmol). The resultant mixture was stirred for 3 h at 5° C. under nitrogen. The reaction mixture was diluted with water (500 mL), extracted with EtOAc (2×750 mL), dried (Na2SO4) and the solvents removed in vacuo to afford the title compound as a yellow oil (12.3 g). extracted with EtOAc (2×750 mL) dried (Na2SO4) the solvents removed in vacuo

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

Procedure: To a solution of 4-hydroxy-3-methylbenzaldehyde (10 g, 73.5 mmol) in dry CH2Cl2 (550 mL) under nitrogen at 5° C. was added tetra-N-butylammonium borohydride (20.58 g, 80 mmol) and the resultant mixture stirred for 1.25 h at 5° C. Saturated ammonium chloride solution (30 mL) was added to the reaction mixture and the resultant mixture stirred for 1 h at 5° C. Saturated ammonium chloride solution (60 mL) was added and the reaction mixture extracted with CH2Cl2, dried (Na2SO4) and the solvents removed in vacuo. Purification by flushing through silica (2×150 g) eluting with EtOAc afforded the title compound as an oily yellow solid (8.01 g). the reaction mixture extracted with CH2Cl2 dried (Na2SO4) the solvents removed in vacuo Purification by flushing through silica (2×150 g) eluting with EtOAc