Borane → 5-Chloro-2-(hydroxymethyl)phenol

HRID 1746100Notes

Reaction equation

HRID 1746100 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([OH:11])[CH:3]=1.B>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 787824-Chlorosalicylic acid

Product 1

HCID 3271485-Chloro-2-(hydroxymethyl)phenolYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chloro-2-hydroxybenzoic acid (Aldrich; 2.0 g, 11.6 mmol) in THF (50 ml) was added dropwise 1 M borane in THF (20.9 ml, 20.9 mmol). The suspension was allowed to stir for 30 min at ambient temperature. The mixture was refluxed at 80° C. for 2.5 h. The solvent was removed in vacuo. The residue was loaded in dichloromethane and purified on silica (100 g) using 0-100% ethyl acetate/cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (1.51 g) as a white solid; LCMS (System 1): (M-H)−=157, tRET=2.44 min.

Workup

  1. temperatureThe mixture was refluxed at 80° C. for 2.5 h
  2. customThe solvent was removed in vacuo
  3. custompurified on silica (100 g)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1654d92c8b614d8baf35161e7c7e7cdb
Source dataset
uspto-grants-2015_10
Patent number
US09149462B2

Reaction notes

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