Ethyl diazoacetate → (2-Phenoxy)ethoxyacetic Acid Ethyl Ester

HRID 2053611

Reaction equation

HRID 2053611 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:18]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 31236Phenoxyethanol

Product 1

HCID 33787264(2-Phenoxy)ethoxyacetic Acid Ethyl EsterYield 82.8%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 2-phenoxyethan-1-ol (1.5 mL, 12.7 mmol) in dichloromethane (50 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.1 mL, 10.5 mmol). The reaction mixture is stirred at rt overnight. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue vacuum distilled to give 1.95 g of the product 440. 1H NMR (CDCl3) δ 7.40-7.25 (m, 2H), 7.10-6.90 (m, 3H), 4.30-4.15 (m, 5H), 4.15-4.05 (m, 1H), 4.05-3.90 (s, 2H), 1.28 (t, 3H)

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-d6f55f5ffb6a416888dd3964d6aa3c44
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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