Dimethyl Sulfoxide → HCID 15097561, compound

HRID 1651220Notes

Reaction equation

HRID 1651220 reaction equation
[H-].[Na+].CS(C)=O.[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:37]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O1CCCC1>[C:38]1([C:37]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 11317723(7-Carboxyheptyl)triphenylphosphonium bromide

Product 1

HCID 15097561HCID 15097561, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out as in Example 87 using the following reagents: sodium hydride (56% dispersion in oil; 8.6 g), dimethylsulfoxide (100 mL), (7-carboxyheptyl)triphenylphosphonium bromide (39.95 g), benzophenone (18.2 g), and tetrahydrofuran (100 mL). The crude acid, isolated in the usual manner, required further purification by HPLC (hexane-ether; 3:2). The appropriate fractions were combined and evaporated and the residue was crystallized from hexane to provide 14.1 g of 9,9-diphenyl-8-nonenoic acid, mp 77.5°-78.5° C. Anal. Calculated for C21H24O2 : C, 81.78; H, 7.84. Found: C, 81.71; H, 7.70.

Workup

  1. customThe crude acid, isolated in the usual manner
  2. custompurification by HPLC (hexane-ether; 3:2)
  3. customevaporated
  4. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-ba3d8758046246e487b8ce28156d54b9
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

Loading…