Dimethyl Sulfoxide → 5,5-Bis(4-methoxyphenyl)-4-pentenoic acid

HRID 1651216Notes

Reaction equation

HRID 1651216 reaction equation
[H-].[Na+].CS(C)=O.[Cl-].[C:8]([CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[CH3:33][O:34][C:35]1[CH:50]=[CH:49][C:38]([C:39]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)=O)=[CH:37][CH:36]=1>O1CCCC1>[CH3:33][O:34][C:35]1[CH:50]=[CH:49][C:38]([C:39]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)=[CH:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70324,4'-DimethoxybenzophenoneHCID 24758Sodium hydrideHCID 21180642(3-Carboxypropyl)(triphenyl)phosphanium chloride

Product 1

HCID 150975605,5-Bis(4-methoxyphenyl)-4-pentenoic acidYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was performed as in Example 87 using sodium hydride (56% dispersion in oil; 9.5 g) dimethylsulfoxide (100 mL), (3-carboxypropyl)triphenylphosphonium chloride (35 g); 4,4'-dimethoxybenzophenone (26.4 g); and tetrahydrofuran (100 mL). After the usual work up, the crude acid was crystallized from dichloromethane-hexane to give 15.6 g of 5,5-bis(4-methoxyphenyl)-4-pentenoic acid, mp 113°-114° C. Anal. Calculated for C19H20O4 : C, 73.06; H, 6.45. Found: C, 73.00; H, 6.45.

Workup

  1. customAfter the usual work up, the crude acid was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-1af6ed33adb34c8b9c02e220d9256f54
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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