3,3-Dimethylglutaric acid → 3,3-Dimethylglutaric acid mono-p-methoxybenzyl ester

HRID 1252220Notes

Reaction equation

HRID 1252220 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][C:4]([OH:6])=[O:5].[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CN(C)C=O.[Cl-].[Na+].C(OCC)(=O)C>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:9][C:8](=[O:10])[CH2:7][C:2]([CH3:11])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 209843,3-Dimethylglutaric acidHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 539055093,3-Dimethylglutaric acid mono-p-methoxybenzyl ester

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,3-dimethylglutaric acid (6.4 g) in dry dimethylformamide (100 ml) was added in four portions sodium hydride (50%) (1.92 g) at 30° to 40° C. under nitrogen atmosphere. The resulting mixture was stirred for 30 minutes, and p-methoxybenzyl chloride (6.28 g) in dry dimethylformamide (20 ml) was added to the mixture. The reaction mixture was stirred at 60° to 70° l C. for 10 hours, diluted with saturated aqueous sodium chloride and ethyl acetate. The ethyl acetate layer was extracted with aqueous potassium carbonate. The aqueous layer was acidified on ice-bath with concentrated hydrochloric acid and extracted with benzene. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give 3,3-dimethylglutaric acid mono-p-methoxybenzyl ester.

Workup

  1. stirringThe reaction mixture was stirred at 60° to 70° l C
  2. waitfor 10 hours
  3. extractionThe ethyl acetate layer was extracted with aqueous potassium carbonate
  4. customThe aqueous layer was acidified on ice-bath with concentrated hydrochloric acid
  5. extractionextracted with benzene
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-c77e434710de4f25b4dc9a65fbab10a5
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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