Toluene → Ethyl 4-(3-bromopropyl)benzoate
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[C:18]1(C)C=CC=C[CH:19]=1>>[CH2:18]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([CH2:4][CH2:3][CH2:2][Br:1])=[CH:6][CH:7]=1)[CH3:19]Participants
4
Procedure
100 g 4-(3-Bromo-propyl)-benzoic acid (JACS 65, 2281 (1943)), 400 ml of toluene and 80 ml of thionyl chloride were refluxed for 4 hours. The solvent and the thionyl chloride in excess were removed under reduced pressure and after addition of 400 ml of absolute ethanol to the residue the mixture was heated for 1 hour to the boiling point. It was evaporated under reduced pressure, the residue was taken up in benzene and washed neutral with a saturated NaHCO3 -solution. The organic phase was distilled off after drying with MgSO4.
Workup
- customThe solvent and the thionyl chloride in excess were removed under reduced pressure
- additionafter addition of 400 ml of absolute ethanol to the residue the mixture
- temperaturewas heated for 1 hour to the boiling point
- customIt was evaporated under reduced pressure
- washwashed neutral with a saturated NaHCO3 -solution
- distillationThe organic phase was distilled off
- dry with materialafter drying with MgSO4
Sources & evidence
- ORD record
- ord-a9c03a3498be42c2a93d10fe5ce8e229
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04097496
Reaction notes
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