4-(2,2-Dimethyl-1-oxopropyl)benzoic acid → 4-(1-Hydroxy-2,2-dimethylpropyl)benzoic acid

HRID 1768671Notes

Reaction equation

HRID 1768671 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([CH3:21])([CH3:20])[C:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)=[O:10]>O1CCCC1>[C:15]([C:14]1[CH:18]=[CH:19][C:11]([CH:9]([C:8]([CH3:21])([CH3:20])[CH3:7])[OH:10])=[CH:12][CH:13]=1)([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 119589814-(2,2-Dimethyl-1-oxopropyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 118203694-(1-Hydroxy-2,2-dimethylpropyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.95 grams (0.051 mole) of lithium aluminum hydride and 30 ml. of tetrahydrofuran is added a solution of 10.5 grams (0.051 mole) of 4-(2,2dimethyl-1-oxopropyl)-benzoic acid in 110 ml. of tetrahydrofuran. The mixture is stirred for 2 hours at 0°-5° C., and then quenched by the addition of sodium sulfate solution. The resulting mixture is made acidic by the cautious add ition of concentrated hydrochloric acid. The mixture is extracted with ether; and the extracts are then washed with 50% brine, dried over magnesium sulfate, filtered and evaporated. The resulting solid is dissolved in aqueous sodium hydroxide, filtered and after acidification with hydrochloric acid, again extracted with ether, dried over magnesium sulfate, filtered and evaporated to yield the title product (m.p. 161.5°-163° C.).

Workup

  1. customquenched by the addition of sodium sulfate solution
  2. additioncautious add ition of concentrated hydrochloric acid
  3. extractionThe mixture is extracted with ether
  4. washand the extracts are then washed with 50% brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe resulting solid is dissolved in aqueous sodium hydroxide
  9. filtrationfiltered
  10. extractionafter acidification with hydrochloric acid, again extracted with ether
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-4ba708e7010f4049b389a0b35c9e404d
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

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