4-Acetamidobenzaldehyde → 4-Acetaminobenzyl alcohol

To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mL) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes:EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mL) and ethyl acetate (4×50 mL) and the organic layer was washed with brine (25 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85%); 1H NMR (DMSO-d6): δ 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H).

1. customthe progress of reaction
2. concentrationthe reaction mixture was concentrated in a rotavap
3. customThe residue was partitioned between water (25 mL) and ethyl acetate (4×50 mL)
4. washthe organic layer was washed with brine (25 mL)
5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
6. customthe removal of the solvent

ORD record

ord-ed173927ef5a4e5db8575b7c022bc0cb

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691787B2