Water → HCID 21519234, compound

HRID 1283129Notes

Reaction equation

HRID 1283129 reaction equation
[OH:1][C:2]1([CH:14]([CH3:18])[C:15](O)=[O:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1.CCOCC>[OH:1][C:2]1([CH:14]([CH3:18])[CH2:15][OH:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 21519247HCID 21519247, compound

Product 1

HCID 21519234HCID 21519234, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 61 grams of 2-(1-hydroxy-2-phenylcyclohexyl)-propionic acid (I) in 200 ml tetrahydrofuran is added dropwise to 30 grams of lithium aluminum hydride in 700 ml ether. After refluxing for 21/2 hours, the mixture is cooled to -5° and treated successively with 140 ml ethyl acetate and 150 ml water. The slurry is filterd, the residue on the filter paper is washed well with ether which is combined wiht the filtrate and the solutin dried over magnesium sulfate. Evaporation of the solution left 57 grams of product (II) melting at 89°-93°C.

Workup

  1. temperatureAfter refluxing for 21/2 hours
  2. temperaturethe mixture is cooled to -5°
  3. washthe residue on the filter paper is washed well with ether which
  4. dry with materialthe solutin dried over magnesium sulfate
  5. customEvaporation of the solution
  6. waitleft 57 grams of product (II) melting at 89°-93°C.

Sources & evidence

ORD record
ord-361da2ff1e0a4be8a3612b28fa638b14
Source dataset
uspto-grants-1976_08
Patent number
US03974157

Reaction notes

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