Benzoyl chloride → HCID 9834203, compound
Reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:7]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1,4-butanediol (18 ml, 0.2 mmol) in pyridine (16 ml), was added slowly at 0° C., under a nitrogen atmosphere, benzoyl chloride (1 ml), 0.1 mmol). After 4 h under stirring at 0° C., the reaction medium was concentrated and the pyridine was eliminated by co-distillation with toluene. The residue was extracted with ether (3×20 ml) and the organic phase was dried (magnesium sulfate), concentrated, and subjected to a flash column chromatography on silica gel (petroleum ether/ethyl acetate 3:2) to give the 4-hydroxybutyl benzoate (9.9 g, 55%) in the form of a colorless oil.
Workup
- concentrationthe reaction medium was concentrated
- extractionThe residue was extracted with ether (3×20 ml)
- dry with materialthe organic phase was dried (magnesium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cf1a1dad707b4d1b8bd62a72a9afd889
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911450B1
Reaction notes
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