Toluene → 12-bromododecanoyl chloride
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O.C1(C)C=CC=CC=1.S(Cl)([Cl:25])=O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([Cl:25])=[O:15]Participants
Procedure
A solution of 30 mmols (8.4 g) of 12-bromododecanoic acid and 10 ml of toluene in 5 ml of thionyl chloride was stirred at 80° C. for 1 hour. Excess thionyl chloride and toluene were distilled out under reduced pressure to obtain 12-bromododecanoyl chloride(acid chloride 9d). A solution of 25 mmols (8.2 g) of hydroxy ester 9c obtained in the above (9-5) was stirred with 30 mmols (3.0 g) of triethylamine in 100 ml of THF. A solution of said acid chloride 9c in THF, was added dropwise thereto followed by stirring for 8 hours. The reaction mixture was extracted with ether, washed with dilute aqueous hydrochloric acid solution, dried, concentrated and then purified by column chromatography to obtain the desired bromo ester 9e (12.1 g, yield 82% [α]23D=+2 35 (chloroform)).
Workup
- distillationExcess thionyl chloride and toluene were distilled out under reduced pressure
Sources & evidence
- ORD record
- ord-9946160fed9b4c81950a5e5fea07af67
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04915867
Reaction notes
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