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

HRID 2232821Notes

Reaction equation

HRID 2232821 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-378cceeaae2d4037b4682d1aad6e55a3
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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