Water → Cyclohexoxyacetic acid

HRID 860472

Reaction equation

HRID 860472 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]([OH:14])=[O:13].O>O1CCCC1>[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 6227Bromoacetic AcidHCID 7966CyclohexanolHCID 24758Sodium hydride

Product 1

HCID 191994Cyclohexoxyacetic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 60% sodium hydride (8.79 g) in tetrahydrofuran (500 mL) was added cyclohexanol (10 g) and the mixture was stirred at 0° C. for 0.5 hour. To the mixture was added bromoacetic acid (13.9 g) under ice-water cooling and the mixture was heated under reflux for 2 hours. After adding water to the mixture and organic solvent was evaporated in vacuo. The aqueous solution was diluted with water, washed with ether, acidified with 1 N hydrochloric acid, and extracted with ether. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo to give (cyclohexyloxy)acetic acid as colorless oil (13.3 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customwas evaporated in vacuo
  4. additionThe aqueous solution was diluted with water
  5. washwashed with ether
  6. extractionextracted with ether
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f8eff3505af434ca1b4dde2b45961d9
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Linked notes

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