Lithium Hydroxide → HCID 10220726, compound

HRID 2119429Notes

Reaction equation

HRID 2119429 reaction equation
[OH:1][CH:2]([C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[C:3]([O:5]CC)=[O:4].[Li+].[OH-]>C1COCC1.O>[OH:1][CH:2]([C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:9])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15839201HCID 15839201, compound

Product 1

HCID 10220726HCID 10220726, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1.75 g (6.2 mmol) of ethyl 2-hydroxy-3,3-diphenylbutyrate were dissolved in 10 ml of THF, and a solution of 0.23 g (9.3 mmol) of LiOH in 6 ml of water was added. The mixture was stirred at room temperature for 16 hours and at 40° C. for 4 hours. The mixture was subsequently concentrated under reduced pressure, taken up in water and washed with ethyl acetate. This was followed by acidification with HCl and extraction three times with ethyl acetate. The combined ethyl acetate phases were dried with MgSO4, and the solvent was stripped off under reduced pressure. The residue was chromatographed on silica gel with CH2Cl2/MeOH (2:1). 0.80 g (50%) of 2-hydroxy-3,3-diphenylbutyric acid was obtained.

Workup

  1. concentrationThe mixture was subsequently concentrated under reduced pressure
  2. washwashed with ethyl acetate
  3. extractionThis was followed by acidification with HCl and extraction three times with ethyl acetate
  4. dry with materialThe combined ethyl acetate phases were dried with MgSO4
  5. customThe residue was chromatographed on silica gel with CH2Cl2/MeOH (2:1)

Sources & evidence

ORD record
ord-8b9ebabd5ab847fc8539eed29b7d4468
Source dataset
uspto-grants-2004_02
Patent number
US06686369B1

Reaction notes

Loading…