Water → 2-Hydroxy-5-methylbenzyl alcohol

HRID 1712401

Reaction equation

HRID 1712401 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([OH:11])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O1CCC[CH2:22]1>>[OH:8][CH2:6][C:5]1[CH:9]=[C:10]([CH3:22])[CH:2]=[CH:3][C:4]=1[OH:11]

Participants

6

Reactant 5

HCID 962Water2×HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 676614-Fluorosalicylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2574522-Hydroxy-5-methylbenzyl alcohol

Procedure

A solution of 4.80 g of 4-fluoro-2-hydroxybenzoic acid in 100 ml of tetrahydrofuran is added dropwise at 0° C. to the suspension of 5.29 g of lithium aluminium hydride in 150 ml of tetrahydrofuran and stirred over 2 hours. The reaction mixture is admixed dropwise successively with 6 ml of water, 6 ml of 15% NaOH and 24 ml of water, and stirred over 1 hour. The mixture is filtered and the filtrate is concentrated by evaporation. The crude title compound is obtained as a red-orange oil from the residue. Rf=0.20 (1:1 EtOAc-heptane); Rt=2.47.

Workup

  1. stirringstirred over 1 hour
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-965226e7585f417aa694817c400d0aa6
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Linked notes

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