4-(Chloromethyl)benzoic acid → [4-(Chloromethyl)phenyl]methanol

HRID 1827981Notes

Reaction equation

HRID 1827981 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.B.C1COCC1>C1COCC1>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 742344-(Chloromethyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 5107660[4-(Chloromethyl)phenyl]methanolYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloromethylbenzoic acid (20 mmol) was dissolved in 20 ml THF, then 30 ml borane/THF were added. The mixture was stirred for 16 hrs at room temperature, and then quenched with excess methanol. Evaporation yielded about 2.5 g 4-chloromethylbenzyl alcohol 36.

Workup

  1. customquenched with excess methanol
  2. customEvaporation

Sources & evidence

ORD record
ord-23054253868843da9ceb969cf16c4ad0
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

Loading…