Sodium Hydroxide → HCID 14631356, compound

HRID 1200274Notes

Reaction equation

HRID 1200274 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][C@@:16]([OH:37])([CH3:36])[C:17]([O:19]C1C(C(C2C=CC=CC=2)(C)C)CCC(C)C1)=[O:18].[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][C@@:16]([OH:37])([CH3:36])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86741635HCID 86741635, compound

Product 1

HCID 14631356HCID 14631356, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.907 g (about 1.35 mmol) of (-)-8-phenylmenthyl (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-hydroxy-2-methylbutanoate in 10 ml of ethanol is treated with 1 ml of 28% sodium hydroxide solution and the mixture is left to stand at room temperature for 16 hours. The mixture is then diluted with 50 ml of water and extracted three times with 50 ml of ether each time. The aqueous phase is acidified (pH 2) with 10% phosphoric acid and extracted three times with 50 ml of ether each time. The combined organic phases are dried over sodium sulphate and the solvent is subsequently removed on a rotary evaporator. There are obtained 212 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-hydroxy-2-methylbutanoic acid.

Workup

  1. waitthe mixture is left
  2. extractionextracted three times with 50 ml of ether each time
  3. extractionextracted three times with 50 ml of ether each time
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customthe solvent is subsequently removed on a rotary evaporator

Sources & evidence

ORD record
ord-7ea6a70644194b7f98e9c4d456eacb99
Source dataset
uspto-grants-1990_02
Patent number
US04904823

Reaction notes

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