3-methyl-2-phenylmethoxyphenol

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

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

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: 2-Benzyloxy-3-methylbenzaldehyde prepared by the above 2-(1) 20.0 g (88.4 mmol) was dissolved in methylene chloride 100 ml and thereto was added m-chloroperbenzoic acid 16.8 g (97.2 mmol). The mixture was reacted at 20° C. under stirring for 10 hours. After disappearance of the raw material, the solution was neutralized with a saturated sodium bicarbonate solution and extracted with methylene chloride. To the extract (2-benzyloxy-3-formyloxytoluene) was added a 10% sodium hydroxide solution 38.9 g (97.2 mmol) in the ice bath and the mixture was stirred for 3 hours. The reaction mixture was neutralized with a 5% hydrochloric acid solution and extracted with methylene chloride. The solvent was removed in vacuo and the residue was purified in the same manner as in the above mentioned 3-(1) to give 2-benzyloxy-3-methylphenol 16.7 g (yield: 88%). The mixture was reacted at 20° C. extracted with methylene chloride To the extract (2-benzyloxy-3-formyloxytoluene) the mixture was stirred for 3 hours extracted with methylene chloride The solvent was removed in vacuo the residue was purified in the same manner as in the

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

Procedure: 2-Benzyloxy-3-methylbenzaldehyde prepared by the above 2-(1) 20.0 g (88.4 mmol) was dissolved in methanol 100 ml and thereto was added sulfuric acid 20.0 g (203 mmol) and then added 30% hydrogen peroxide 30.1 g (265 mmol). The mixture was refluxed for 2 hours. After disappearance of the raw material, the solution was concentrated in vacuo, neutralized with a saturated sodium bicarbonate solution and extracted with methylene chloride. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate) to give 2-benzyloxy-3-methylphenol 13.3 g (yield: 70%). The mixture was refluxed for 2 hours After disappearance of the raw material, the solution was concentrated in vacuo extracted with methylene chloride The solvent was removed in vacuo the residue was purified by silica gel chromatography (n-hexane-ethyl acetate)