Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14347264, compound

HRID 1110557Notes

Reaction equation

HRID 1110557 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[CH:10][CH:11]=O.[C:21]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH3:24])=[O:22]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:24][O:23][C:21](=[O:22])/[CH:25]=[CH:11]/[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14347228HCID 14347228, compound

Product 1

HCID 14347264HCID 14347264, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

In the manner described in Example 99, 3,3-bis(2-methoxyphenyl) -2-propenal (7.1 g) was reacted with (carbomethoxymethylene) triphenylphosphorane (9.7 g) in carbon tetrachloride (60 ml) and dichloromethane (20 mL) for 3 days at room temperature and then overnight at reflux. The crude ester isolated in the normal manner was crystallized from 2-propanol-hexane to yield 6.5 g of (E)-5,5-bis(2-methoxyphenyl)-2,4-pentadienoic acid methyl ester, mp 100°-102° C. A portion was recrystallized from the same solvents to furnish the analytical sample, mp 101°-102° C.

Workup

  1. temperatureovernight at reflux
  2. customThe crude ester isolated in the normal manner
  3. customwas crystallized from 2-propanol-hexane

Sources & evidence

ORD record
ord-1f5286f03631449dbeb47ec29ab9990b
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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