Water → HCID 22054031, compound

HRID 1830122Notes

Reaction equation

HRID 1830122 reaction equation
C([O:3][C:4](=[O:22])[CH:5]([CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C.O1CCOCC1.[OH-].[Na+].O>C(O)C>[CH2:15]([S:14][CH2:13][CH:5]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:4]([OH:22])=[O:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 69437662HCID 69437662, compound

Product 1

HCID 22054031HCID 22054031, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-benzylsulfanylmethyl-3-cyclohexyl-propionic acid ethyl ester (0.230 g), dioxane (10 mL), sodium hydroxide (1N, 3 mL), water (2 mL) and ethanol (4 mL) was stirred for 20 hours at room temperature. The solvents were evaporated and the residue dissolved in water (50 mL). The aqueous solution was washed twice with ether and then acidified to pH2. The product was extracted from the aqueous solution with ethyl acetate and the extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure to give acid 2-benzylsulfanylmethyl-3-cyclohexyl-propionic acid (0.210 g).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue dissolved in water (50 mL)
  3. washThe aqueous solution was washed twice with ether
  4. extractionThe product was extracted from the aqueous solution with ethyl acetate
  5. washthe extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed by rotary evaporation at reduced pressure

Sources & evidence

ORD record
ord-f147e516923445c98674d91a4614f6f1
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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