Sodium Hydroxide → 3,3-Difluoro-3-(4-fluorophenyl)propan-1-ol

To a solution of acetic acid [3,3-difluoro-3-(4-fluorophenyl)-propyl]ester (5.50 g, 23.7 mmol) in ethanol (70 ml) is added 35% aqueous sodium hydroxide (20 ml) at 0° C. and the reaction mixture is stirred at RT for 1 h. After completion of reaction, the solvent is evaporated and the residue is diluted with water (150 ml) and acidified with aqueous hydrochloric acid before extraction with EtOAc (3×100 ml). The combined organic layers are washed with water (150 ml), brine (150 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield 3,3-difluoro-3-(4-fluorophenyl)-propan-1-ol (4.30 g, 22.6 mmol, 95%).

1. customAfter completion of reaction
2. customthe solvent is evaporated
3. additionthe residue is diluted with water (150 ml)
4. extractionacidified with aqueous hydrochloric acid before extraction with EtOAc (3×100 ml)
5. washThe combined organic layers are washed with water (150 ml), brine (150 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated in vacuo
8. customto get the crude product, which
9. customis purified by column chromatography (silica gel, 10% EtOAc/hexane)

ORD record

ord-da568cd3f4eb4cba98391a05b7bdb48a

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284286B2