Borane → 2-Chloro-3-(hydroxymethyl)phenol
Reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B>O1CCCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][C:10]=1[OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 2-chloro-3-hydroxybenzoic acid (2.59 g, 15 mmol) in tetrahydrofuran was added dropwise to a solution of borane (48 mmol) in tetrahydrofuran (150 mL) at a temperature of 0° C. The reaction mixture was then warmed to 60° C. and allowed to stir overnight. Upon cooling, the mixture was quenched with water and made basic with 3M sodium hydroxide. The aqueous layer was separated, acidified with 3M hydrochloric acid, and extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Recrystallization from ethanol/hexane gave 2-chloro-3-hydroxymethylphenol as a white crystalline solid (1.63 g, 64.8%).
Workup
- temperatureUpon cooling
- customthe mixture was quenched with water
- customThe aqueous layer was separated
- extractionextracted with dichloromethane
- dry with materialThe combined organic extracts were dried over sodium sulfate
- concentrationconcentrated in vacuo
- customRecrystallization from ethanol/hexane
Sources & evidence
- ORD record
- ord-95cd191f1bde48978fe24fd5a39c0d6d
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06335459B1
Reaction notes
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