3-(Methoxycarbonyl)benzoic acid → Benzoic acid, 3-(hydroxymethyl)-, methyl ester

HRID 2175250Notes

Reaction equation

HRID 2175250 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])=[O:4]>C1COCC1.CCOC(C)=O>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 1

HCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 155058Benzoic acid, 3-(hydroxymethyl)-, methyl esterYield 86.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(methoxycarbonyl)benzoic acid (0.200 g, 1.11 mmol) in THF (6.0 mL) at 0° C. was added borane tetrahydrofuran complex (5.55 mL, 5.55 mmol) slowly. The reaction mixture was slowly warmed to room temperature and stirred at for 3 h. After this time, the reaction mixture was diluted with EtOAc and quenched very slowly with water. The organic layer was separated, washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (0.16 g, 84% yield) as a colorless oil. LCMS, [M+H]+=167.0.

Workup

  1. customquenched very slowly with water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8010e90db90844e0868ee85e91da6c98
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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