Water → Methyl 2-chloro-4-(hydroxymethyl)benzoate

HRID 2270864Notes

Reaction equation

HRID 2270864 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O-])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].O.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 212765331,4-Benzenedicarboxylic acid, 2-chloro-, 1-methyl ester

Product 1

HCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (10 M; 10 mL, 100 mmol) was added to a solution of 2-chloro-1,4-benzenedicarboxylic acid, 1-methyl ester (Example 1; 11.98 g, 55.8 mmol) in tetrahydrofuran (100 mL). The solution was heated at reflux for 2 h and then allowed to stand at room temperature overnight. It was poured into water and ethyl acetate (200 mL each). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with brine (200 mL), dried (MgSO4), filtered, and evaporated to give 2-chloro-4-(hydroxymethyl)benzoic acid, methyl ester (11.09 g, 99%) as a colorless oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  5. washThe combined organic layers were washed with brine (200 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3fb27dafc26a4ec0b365663259503d32
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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