Methanol → (Cyclohexylmethoxy)acetic Acid Ethyl Ester

HRID 2053605Notes

Reaction equation

HRID 2053605 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-].CO>ClCCl.CCOCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:16]

Participants

7

Reactant 3

HCID 887MethanolHCID 7507CyclohexanemethanolHCID 12192Ethyl diazoacetate

Product 1

HCID 57278482(Cyclohexylmethoxy)acetic Acid Ethyl EsterYield 100.9%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclohexylmethanol (1.23 mL, 10.0 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at RT for 30 min. To the reaction mixture is added MeOH, and the reaction mixture is rotary evaporated, and the residue dissolved in Et2O, filtered through celite, and the filtrate is evaporated and the residue is vacuum distilled at to give 2.02 g of the product 419. 1H NMR (CDCl3) δ 4.22 (q, 2H), 4.05 (s, 2H), 3.33 (d, 2H), 1.8-1.5 (m, 7H), 1.4-1.1 (m, 5H), 1.1-0.9 (m, 2H); MS: m/z 200 (M++1).

Workup

  1. filtrationfiltered through celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at

Sources & evidence

ORD record
ord-7db69edbe5b3426ba3d0a59cd92ba3e5
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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