Sodium Hydroxide → Cyclohexyl-hydroxy-thiophen-2-yl-acetic acid

HRID 660079Notes

Reaction equation

HRID 660079 reaction equation
C([O:3][C:4](=[O:18])[C:5]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([OH:11])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)C.[OH-].[Na+]>CO.C1COCC1>[CH:12]1([C:5]([OH:11])([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:18])=[O:3])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44147725Ethyl cyclohexyl(hydroxy)(thiophen-2-yl)acetate

Product 1

HCID 13063448Cyclohexyl-hydroxy-thiophen-2-yl-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclohexyl-hydroxy-thiophen-2-yl-acetic acid ethyl ester (361.8 g, 1.35 mol) in MeOH (1.5 litres) and THF (1.5 litres) is treated portionwise with 2M NaOH (1.1 litres) over 30 minutes. The reaction mixture is stirred at room temperature overnight and then concentrated in vacuo to remove the organic solvents. The remaining aqueous portion is partitioned between EtOAc (2 litres) and 20% citric acid in water (1 litre). The organic layer is separated, washed with brine and concentrated in vacuo to afford the titled compound which is used crude in the next step.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the organic solvents
  3. customThe remaining aqueous portion is partitioned between EtOAc (2 litres) and 20% citric acid in water (1 litre)
  4. customThe organic layer is separated
  5. washwashed with brine
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0eac8a6a63d42b58f0615e03b6d484d
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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