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

HRID 2232819Notes

Reaction equation

HRID 2232819 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)-2,4hexadienoic acid methyl ester, mp 84°-86° C.

Sources & evidence

ORD record
ord-7750132a6293448b8d1ad744c905485d
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

Loading…