Dimethyl Sulfate → 2-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-1-methoxy-3,5,5,8,8-pentamethyl-

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Reaction Steps

Methylation. A solution of sodium hydroxide (0.98 g, 0.0244 mol) in water (24 mL) was added in one portion to a solution of 2-formyl-1-hydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (3 g, 0.0122 mol), dimethyl sulfate (3.07 g, 0.0244 mol) and Adogen 464* (0.56 g) in methylene dichloride (48 mL). The mixture was stirred vigorously at 38°-40° C. for 4 h. After cooling, the organic layer was separated, washed with brine (3×20 mL) and dried (Na2SO4). The solvent was removed by distillation and the residue was distilled to yield 2-formyl-1-methoxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (3a), (2.5 g), mp 78° C. (from hexane), GLC purity 99.7%, exhibiting the expected spectral data.

Provenance & Evidence