Hydrochloric Acid → (3-Chloro-5-methoxyphenyl)methanol

To an ice-cold solution of 3-chloro-5-methoxybenzaldehyde (27 mmol, 4.60 g) in ethanol (90 ml) was added NaBH4 (30 mmol, 1.14 g) in one portion under stirring. After 0.5 h the mixture was allowed to reach room temperature and stirred for another 0.5 h. HCl (2 M, ˜25 ml)) was added slowly until no more hydrogen gas evolved, the resulting mixture was concentrated under reduced pressure and the residue separated between water and ether, the organic phase was washed with braine and dried (MgSO4). Filtration and evaporation of solvents afforded the title compound (4.53 g, 97%) as a white solid. The product was used without further purification in the next step. An analytically pure sample was obtained be means of flash chromatography (silica, hexane/ether grad.). 1H NMR (CDCl3, 500 MHz) δ 2.77 (br, 1H), 3.76 (s, 3H), 4.55 (s, 2H), 6.74 (s, 1H), 6.77 (s, 1H) and 6.88 (s, 1H).

1. customto reach room temperature
2. stirringstirred for another 0.5 h
3. concentrationthe resulting mixture was concentrated under reduced pressure
4. customthe residue separated between water and ether
5. washthe organic phase was washed with braine
6. dry with materialdried (MgSO4)
7. filtrationFiltration and evaporation of solvents

ORD record

ord-33c7b7b96c5d4a71b83aae02763d98c3

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799947B2