1,2-Epoxybutane → HCID 53687838, compound
Reaction equation
[Cl-].[Cl:2][C:3]1[C:4]([CH3:31])=[C:5]([C:26]([CH3:30])=[CH:27][C:28]=1[CH3:29])[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:32]([O:36][C:37](=[O:48])[CH:38]=[C:39]([CH3:47])[CH:40]=[CH:41][CH:42]=[C:43]([CH:45]=O)[CH3:44])[CH2:33][CH2:34][CH3:35].C1OC1CC>>[CH2:32]([O:36][C:37](=[O:48])[CH:38]=[C:39]([CH3:47])[CH:40]=[CH:41][CH:42]=[C:43]([CH3:45])[CH:44]=[CH:6][C:5]1[C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:3]([Cl:2])[C:4]=1[CH3:31])[CH2:33][CH2:34][CH3:35]Participants
4
Procedure
16 g of 3-chloro-2,4,6-trimethyl-benzyl-triphenylphosphonium chloride and 10 g of 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid butyl ester are heated to boiling with stirring after the addition of 40 g of 1,2-butylene oxide. The 1,2-butylene oxide is slowly distilled off. The reaction mixture is stirred for 30 minutes at 80°-82° C, then cooled and thoroughly extracted with hexane. The hexane extract is shaken out 5 times with 50 ml of methanol/water 70:30 parts by volume each time, then dried over sodium sulphate and evaporated under reduced pressure to produce 9-(3-chloro-2,4,6-trimethyl-phenyl),3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid butyl ester as a residue.
Workup
- distillationThe 1,2-butylene oxide is slowly distilled off
- stirringThe reaction mixture is stirred for 30 minutes at 80°-82° C
- temperaturecooled
- extractionthoroughly extracted with hexane
- extractionThe hexane extract
- stirringis shaken out 5 times with 50 ml of methanol/water 70:30 parts by volume each time
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-e8f98d36bce94fefbf6a276234a1a32d
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04105681
Reaction notes
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