3-Hydroxy-2-methylbenzoic Acid → 3-(Hydroxymethyl)-2-methylphenol

HRID 2240351Notes

Reaction equation

HRID 2240351 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6]>O1CCCC1>[OH:6][CH2:5][C:4]1[C:3]([CH3:11])=[C:2]([OH:1])[CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 130594263-(Hydroxymethyl)-2-methylphenolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-2-methyl-benzoic acid (1.0 g, 7.2 mmol) in tetrahydrofuran (80 mL) was treated with dropwise added BH3-tetrahydrofuran (1M in tetrahydrofuran) (10 mL). The reaction mixture was stirred at rt overnight. Quenched with 10% NaOH, the mixture was adjusted pH to 7 with 10% HCl and extracted with isopropanol/dichloromethane (1:3) (2×), The organic layers were combined and washed with water, brine, dried to afford the title compound (795 mg, 80%). MS (DCI/NH3) m/z 139 (M+1)+.

Workup

  1. customQuenched with 10% NaOH
  2. extractionextracted with isopropanol/dichloromethane (1:3) (2×)
  3. washwashed with water, brine
  4. customdried

Sources & evidence

ORD record
ord-14194e9f5fca4fefa9d29b0a2bf9d60b
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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