Sodium Hydroxide → HCID 14631356, compound

HRID 653200Notes

Reaction equation

HRID 653200 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-b3e30a7de7e8457dbe8273d49cd555fa
Source dataset
uspto-grants-1987_06
Patent number
US04675421

Reaction notes

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