Hexane → 4'-Methoxyacetophenone

Participants

Reaction Conditions

Reaction Steps

To a vial was added wet Raney Ni 4200 (8 mg, 7×10−5 mol, 50 mol %) then 3 mL hexane followed by 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol (38 mg, 1.4×10−4 mol) and of NaBH4 (3 mg, 7×10−5 mol, 50 mol %). The vial was capped and heated to 80° C. for 24 hours. The reaction was cooled, opened and 10 mg of NH4COOH was added. 50 mL of Et2O was used to transfer the crude to an erlenmeyer containing MgSO4. After drying the solution was filtered and concentrated. HNMR gave 63% conversion to 1-(4-methoxyphenyl)ethan-1-one and 1-(4-methoxyphenyl)ethan-1-ol in a ratio 3:7. 63% of the β-O-4 bond was broken.

Provenance & Evidence