Methanol → Methyl 4-(chloromethyl)benzoate

HRID 1458679Notes

Reaction equation

HRID 1458679 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:17])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 742344-(Chloromethyl)benzoic acid

Product 1

HCID 36664Methyl 4-(chloromethyl)benzoate

Procedure

A solution of 2.0 g (12 mmol) of 4-chloromethylbenzoic acid in 50 ml of methanol was added with 5 droplets of concentrated sulfuric acid, followed by stirring under heat and reflux for 4 days. After neutralization with a 5% aqueous solution of sodium carbonate, the resultant mixture was extracted with chloroform. The chloroform extract was dried over magnesium sulfate and then concentrated under reduced pressure, whereby 1.7 g of a colorless liquid were obtained.

Workup

  1. temperatureunder heat
  2. temperaturereflux for 4 days
  3. extractionAfter neutralization with a 5% aqueous solution of sodium carbonate, the resultant mixture was extracted with chloroform
  4. extractionThe chloroform extract
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c3e198d07f64efba424ca7664ae5c00
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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