Reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:17][CH:18](O)[CH3:19].C1C[O:24]CC1>>[C:1]([O:8][CH2:19][CH2:18][Cl:17])(=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Procedure
20.0 g (142 mM) of benzoyl chloride and then additionally 14.4 g (142 mM) of triethylamine were added dropwise with vigorous stirring at room temperature to a solution of 11.5 g (142 mM) of chloroethanol in 200 ml of THF (exothermic reaction). After stirring for 1 h, the mixture was concentrated on a rotary evaporator, and the residue was partitioned between methylene chloride and water and acidified with 10% strength hydrochloric acid. The aqueous phase was reextracted twice with methylene chloride and the organic phase was then concentrated after drying with sodium sulfate. 26.0 g (99%) of 2-chloroethyl benzoate were isolated.
Workup
- concentrationthe mixture was concentrated on a rotary evaporator
- customthe residue was partitioned between methylene chloride and water
- concentrationthe organic phase was then concentrated
- dry with materialafter drying with sodium sulfate
Sources & evidence
- ORD record
- ord-c5ebfe6e19984f1aabaa307bac8ba7d0
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616705
Linked notes
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