Hydrochloric Acid → Cyclohexoxyacetic acid

HRID 56265

Reaction equation

HRID 56265 reaction equation
[OH-].[Na+].[CH:3]1([O:9][CH2:10][C:11]([O:13]CC)=[O:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>O.CO>[CH:3]1([O:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 93856Ethyl (cyclohexyloxy)acetate

Product 1

HCID 191994Cyclohexoxyacetic acidYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of NaOH (4.89 g, 122 mmol) in a mixture of water (20 mL) and MeOH (20 mL) in an ice bath was added a solution of ethyl 2-(cyclohexyloxy)acetate (3.8 g, 20.4 mmol) in MeOH (10 mL) slowly and the mixture was stirred at rt for 2 h. It was then acidified to pH 4 with concentrated hydrochloric acid and extracted with DCM (20 mL×2). The combined organic layers were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as pale yellow oil (2.7 g, 84%).

Workup

  1. extractionextracted with DCM (20 mL×2)
  2. washThe combined organic layers were washed with brine (40 mL×2)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-74a1e08e410b41e390b42a7a8940f57f
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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