Water → [4-(Aminomethyl)phenyl]methanol

To a stirred suspension of LiAH4 (285 mg, 7.52 mmol) in diethylether (10 mL) at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2) gave 152 mg (29%) of 4-(aminomethyl)benzylalcohol (57 MBT52B) as a white solid. Rf=0.51 (30% MeOH in CH2Cl2+3.5% NH4OH).

1. temperatureThe grey reaction mixture was heated
2. temperatureto reflux for 3 h
3. filtrationThe resulting white slurry was filtered
4. washwashed with CH2Cl2 (20 mL)
5. extractionExtraction
6. customwith additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation
7. customyielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2)

ORD record

ord-68ed2918fd074090952aebdb54b4e439

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06815458B2