Methanol → 2-[2-(2-Chlorophenoxy)ethoxy]acetic Acid Ethyl Ester

HRID 2053610

Reaction equation

HRID 2053610 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-].CO>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[Cl:1])[CH3:19]

Participants

6

Reactant 3

HCID 887MethanolHCID 12192Ethyl diazoacetateHCID 849332-(2-Chlorophenoxy)ethanol

Product 1

HCID 685707682-[2-(2-Chlorophenoxy)ethoxy]acetic Acid Ethyl EsterYield 52.6%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 2-(2-chlorophenoxy)ethanol (1.73 mL, 10.0 mmol) in dichloromethane (20 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 20 min. To the reaction mixture is added MeOH followed by rotary evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (25:75) gives 1.36 g of the product 436. 1H NMR (CDCl3) δ 7.35 (d, 1H), 7.19 (d, 1H), 6.95-6.90 (m, 2H), 4.30 (s, 2H), 4.25-4.15 (m, 4H), 4.0 (t, 2H), 1.2 (t, 3H); MS: m/z 259 (M++1).

Workup

  1. customthe residue is purified by chromatography on silica gel
  2. washelution with EtOAc:heptane (25:75)

Sources & evidence

ORD record
ord-abacd520fa7a45a4a3d6e9e6442ca255
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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