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

HRID 393098Notes

Reaction equation

HRID 393098 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-81e3bf505df149e29f8c9a6753e74dee
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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