Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoate → 9-(4-Methoxy-3,5-diethyl-2,6-dimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

HRID 27859Notes

Reaction equation

HRID 27859 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[C:29]([CH2:30][CH3:31])=[C:28]([CH3:32])[C:7]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:6]([CH3:33])[C:5]=1[CH2:34][CH3:35].[CH2:36]([O:38][C:39](=[O:50])[CH:40]=[C:41]([CH3:49])[CH:42]=[CH:43][CH:44]=[C:45]([CH:47]=O)[CH3:46])[CH3:37]>>[CH2:36]([O:38][C:39](=[O:50])[CH:40]=[C:41]([CH3:49])[CH:42]=[CH:43][CH:44]=[C:45]([CH3:47])[CH:46]=[CH:8][C:7]1[C:6]([CH3:33])=[C:5]([CH2:34][CH3:35])[C:4]([O:3][CH3:2])=[C:29]([CH2:30][CH3:31])[C:28]=1[CH3:32])[CH3:37]

Participants

3

Reactant 2

HCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoateHCID 867359074-Methoxy-3,5-diethyl-2,6-dimethyl-benzyl-triphenylphosphonium chloride

Product 1

HCID 542034379-(4-Methoxy-3,5-diethyl-2,6-dimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

Procedure

4-methoxy-3,5-diethyl-2,6-dimethyl-benzyl-triphenylphosphonium chloride is condensed with 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid ethyl ester to produce the 9-(4-methoxy-3,5-diethyl-2,6-dimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester which is converted by the procedure of Example 7 to 9-(4-methoxy-3,5-diethyl-2,6-dimethyl-phenyl)acid, m.p: 153°-154° C.

Sources & evidence

ORD record
ord-deccb74f8df04c5aa4ad7431e9e329a1
Source dataset
uspto-grants-1980_09
Patent number
US04224244

Reaction notes

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