1,2-Epoxybutane → HCID 54347864, compound
Reaction equation
[Cl-].[Cl:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([Cl:31])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:32]([O:34][C:35](=[O:46])[CH:36]=[C:37]([CH3:45])[CH:38]=[CH:39][CH:40]=[C:41]([CH:43]=O)[CH3:42])[CH3:33].C1OC1CC>>[CH2:32]([O:34][C:35](=[O:46])[CH:36]=[C:37]([CH3:45])[CH:38]=[CH:39][CH:40]=[C:41]([CH3:43])[CH:42]=[CH:5][C:4]1[C:25]([Cl:31])=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:3]=1[Cl:2])[CH3:33]Participants
4
Procedure
39 g. of 2,6-dichloro-4-methoxy-benzyl-triphenylphosphonium chloride and 16 g. of 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid ethyl ester are heated at 82°-85° C. under reflux conditions while stirring for 2 hours after the addition of 40 g. of 1,2-butylene oxide. The mixture is then thoroughly extracted with hexane. The hexane extract is washed several times with methanol/water (60:40 parts by volume), dried over sodium sulphate and evaporated under reduced pressure. The residue is purified by absorption on silica gel using hexane for the elution. The 9-(2,6-dichloro-4-methoxy-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester obtained from the eluate melts at 117°-118° C. after recrystallisation from hexane.
Workup
- additionafter the addition of 40 g
- extractionThe mixture is then thoroughly extracted with hexane
- extractionThe hexane extract
- washis washed several times with methanol/water (60:40 parts by volume)
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
- customThe residue is purified by absorption on silica gel
- washfor the elution
Sources & evidence
- ORD record
- ord-768e756cf50d487f9033ad003dcdb8c7
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04187247
Reaction notes
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