Methanol → 4,4-Dimethyl-5-phenylpentanoic acid

HRID 1610657Notes

Reaction equation

HRID 1610657 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[Na+].O.CO>O1CCCC1>[CH3:1][C:2]([CH3:17])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 10879068Ethyl 4,4-dimethyl-5-phenylpentanoate

Product 1

HCID 222615154,4-Dimethyl-5-phenylpentanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4,4-dimethyl-5-phenylpentanoate (45.47 g, 194.0 mmol) and sodium hydroxide (15.5 g, 388 mmol), water (200 ml), methanol (200 ml) and tetrahydrofuran (100 ml) was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure and diluted with water. After washing with diethyl ether, the mixture was acidified with conc. hydrochloric acid and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate) to give the objective substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with water
  3. washAfter washing with diethyl ether
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography (ethyl acetate)
  9. customto give the objective substance

Sources & evidence

ORD record
ord-06f99d3c121b49e1adb099b488b1d294
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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