Toluene → Gemfibrozil

HRID 978803

Reaction equation

HRID 978803 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([CH3:14])([CH3:13])[C:6]([O:8]CC(C)C)=[O:7].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[O-:23].[Na+].C1(C)C=CC=CC=1>CS(C)=O>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[O:23][CH2:2][CH2:3][CH2:4][C:5]([CH3:14])([CH3:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 139137102-Methylpropyl 5-chloro-2,2-dimethylpentanoateHCID 23672785Sodium 2,5-dimethylphenolate

Product 1

HCID 3463GemfibrozilYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

subsequently reacting said 2-methylpropyl 5-chloro-2,2-dimethylpentanoate with sodium 2,5-dimethylphenolate under reflux in a solvent comprising a mixture of from 10 parts (V/V) toluene/1 part (V/V) dimethylsulfoxide to 5 parts (V/V) toluene/1 part (V/V) dimethylsulfoxide, hydrolyzing the resulting ester, and thereafter acidifying the mixture and isolating 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid;

Workup

  1. temperatureunder reflux in a solvent comprising

Sources & evidence

ORD record
ord-236b92105dd24bb1a6f646a20ccc4c94
Source dataset
uspto-grants-1987_05
Patent number
US04665226

Linked notes

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