Cyclohexanol → Ethyl (cyclohexyloxy)acetate

HRID 56264

Reaction equation

HRID 56264 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>C(Cl)Cl>[CH:1]1([O:7][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 12192Ethyl diazoacetate

Product 1

HCID 93856Ethyl (cyclohexyloxy)acetateYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of cyclohexanol (2.40 g, 24.0 mmol) and Rh2(OAc)4 (50 mg, 0.11 mmol) in DCM (50 mL) was added ethyl 2-diazoacetate (2.73 g, 23.9 mmol) and the mixture was stirred at rt for 5 min. It was then filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1) to give the title compound as colorless oil (3.8 g, 85%).

Workup

  1. filtrationIt was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1)

Sources & evidence

ORD record
ord-96feca54d1cd4875a1808baba4200b04
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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