Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14347287, compound

HRID 1110571Notes

Reaction equation

HRID 1110571 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH3:13])=[CH:10]/[CH:11]=O)=[CH:5][CH:4]=1.[C:14]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH3:17])=[O:15]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:17][O:16][C:14](=[O:15])/[CH:18]=[CH:11]/[CH:10]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[CH3:13]

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 13108371HCID 13108371, compound

Product 1

HCID 14347287HCID 14347287, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (E)-3-(4-methoxyphenyl)-2-butenal (8 g) was treated with (carbomethoxymethylene)triphenylphosphorane (17 g) in carbon tetrachloride (70 mL) and dichloromethane (15 mL) overnight at room temperature. The ester was isolated in the normal fashion and crystallized from hexane to afford 7.2 g of (E,E)-5-(4-methoxyphenyl)-2,4-hexadienoic acid methyl ester, mp 84°-86° C.

Sources & evidence

ORD record
ord-216004e4dfcb4d789a4d0ae5dd71e8dc
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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