Water → Methyl 3-(2-chloroethoxy)benzoate

HRID 1510135Notes

Reaction equation

HRID 1510135 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[Cl:18][CH2:19][CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O.O>CN(C=O)C>[Cl:18][CH2:19][CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 43532224Methyl 3-(2-chloroethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-hydroxybenzoate (10.0 g, 65.7 mmol) in DMF (100 mL) was added potassium carbonate (18.17 g, 131.4 mmol) and 2-chloroethyl-p-toluenesulfonate (15.7 g, 67.0 mmol). After stirring at 60° C. overnight the reaction mixture was poured into H2O, extracted with ethyl acetate (three times), dried over MgSO4 and concentrated under vacuum. Purification by silica gel chromatography (10% EtOAc/hexanes) afforded the desired product.

Workup

  1. extractionextracted with ethyl acetate (three times)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-40078a2c4d4648e89cae4e76cde8fc2b
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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