Water → Cyclohexoxyacetic acid

HRID 1429448

Reaction equation

HRID 1429448 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:11][C:12]([O:14]CC)=[O:13].O>CN(C=O)C>[CH:3]1([O:9][CH2:11][C:12]([OH:14])=[O:13])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 7966CyclohexanolHCID 24758Sodium hydride

Product 1

HCID 191994Cyclohexoxyacetic acidYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound NaH (719 mg, 29.94 mmol) in DMF (10 mL) was added cyclohexanol (1 g, 9.98 mmol) at 0° C. After stirring for 5 minutes, ethyl 2-bromoacetate (2 g, 11.98 mmol) was added and the mixture stirred for another 16 h. Once complete, the mixture was treated with water (50 mL) and washed with ethyl acetate (2×20 mL). The water layer was treat with 2N HCL until pH 3. The water layer was extracted with ethyl acetate (2×20 ml) and the combined organic layers washed with brine (30 mL), dried over Na2SO4 and concentrated to give the desired product (500 mg, 27.8%) as colorless oil which was used in next step without further purification.

Workup

  1. stirringthe mixture stirred for another 16 h
  2. washwashed with ethyl acetate (2×20 mL)
  3. additionThe water layer was treat with 2N HCL until pH 3
  4. extractionThe water layer was extracted with ethyl acetate (2×20 ml)
  5. washthe combined organic layers washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3b552c876dff45edb98b70decfbfa6a1
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Linked notes

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