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

HRID 27860Notes

Reaction equation

HRID 27860 reaction equation
[Cl-].[CH2:2]([O:5][C:6]1[CH:31]=[C:30]([CH3:32])[C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:8]([CH3:33])[C:7]=1[CH3:34])[CH2:3][CH3:4].[CH2:35]([O:37][C:38](=[O:49])[CH:39]=[C:40]([CH3:48])[CH:41]=[CH:42][CH:43]=[C:44]([CH:46]=O)[CH3:45])[CH3:36]>>[CH2:35]([O:37][C:38](=[O:49])[CH:39]=[C:40]([CH3:48])[CH:41]=[CH:42][CH:43]=[C:44]([CH3:46])[CH:45]=[CH:10][C:9]1[C:30]([CH3:32])=[CH:31][C:6]([O:5][CH2:2][CH2:3][CH3:4])=[C:7]([CH3:34])[C:8]=1[CH3:33])[CH3:36]

Participants

3

Reactant 2

HCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoateHCID 867359094-Propoxy-2,3,6-trimethyl-benzyl-triphenyl-phosphonium chloride

Product 1

HCID 539413659-(4-Propoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

Procedure

4-propoxy-2,3,6-trimethyl-benzyl-triphenyl-phosphonium chloride is condensed with 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid ethyl ester to produce 9-(4-propoxy-2,3,6-trimethyl-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-propoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid, m.p.: 200°-201° C.

Sources & evidence

ORD record
ord-75216350ef6b4490a87c4ec3f64121cd
Source dataset
uspto-grants-1980_09
Patent number
US04224244

Reaction notes

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