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

HRID 401205Notes

Reaction equation

HRID 401205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5](O)=[O:6].O.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 143722353-Chloro-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
76 °C

Procedure

To a solution of 3-chloro-4-(methoxycarbonyl)benzoic acid (400 mg, 1.9 mmol) in anhydrous THF (15 mL) was added Borane methyl sulfide complex (10 M, 0.56 mL, 5.6 mmol). The resulting solution was heated at 76° C. for 6 hours. After being cooled, the mixture was slowly poured into water (40 mL) at −10° C., then followed a standard aqueous/EtOAc workup procedure to give crude product (350 mg, yield 94%).

Workup

  1. temperatureAfter being cooled

Sources & evidence

ORD record
ord-b3d1fc3fe6104007af670439b1414bed
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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