Dichloromethane → 5-Pentyl-2,4-decadienoic acid methyl ester

HRID 2232845Notes

Reaction equation

HRID 2232845 reaction equation
[CH2:1]([C:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:8]=O)[CH2:2][CH2:3][CH2:4][CH3:5].[C:15]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:17][CH3:18])=[O:16].ClCCl>C(Cl)(Cl)(Cl)Cl>[CH3:18][O:17][C:15](=[O:16])[CH:19]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 145472433-Pentyl-2-octenal

Product 1

HCID 540561795-Pentyl-2,4-decadienoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

As described in Example 99, 3-pentyl-2-octenal (7.85 g) was treated with (carbomethoxymethylene)triphenylphosphorane (15.3 g) in carbon tetrachloride (100 mL) containing dichloromethane (50 mL) for 3 days at room temperature. The usual work up furnished 10.1 g of 5-pentyl-2,4-decadienoic acid methyl ester which was then saponified in a refluxing mixture of methanol (40 mL) and 2N NaOH (30 mL). After 1 hour the acid was isolated in the usual way to give 8.15 g of 5-pentyl-2,4-decadienoic acid as an oil.

Sources & evidence

ORD record
ord-5be5213ab79c4040ad3b53f621d52405
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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