Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86742576, compound

HRID 1110573Notes

Reaction equation

HRID 1110573 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH2:13][CH3:14])=[CH:10]/[CH:11]=O)=[CH:5][CH:4]=1.[C:15]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:17][CH3:18])=[O:16]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:18][O:17][C:15](=[O:16])/[CH:19]=[CH:11]/[CH:10]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14547233HCID 14547233, compound

Product 1

HCID 86742576HCID 86742576, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (E)-3-(4-methoxyphenyl)-2-pentenal (7.1 g) was treated with (carbomethoxymethylene)triphenylphosphorane (14 g) in carbon tetrachloride (70 mL) and dichloromethane (15 mL) overnight at room temperature. The ester was isolated in the normal fashion to afford 8 g of (E,E)-5-(4-methoxyphenyl)-2,4-heptadienoic acid methyl ester as an oil.

Sources & evidence

ORD record
ord-b823a41a28834eda9c4ff4cbf0b84320
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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