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

HRID 18820

Reaction equation

HRID 18820 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, 2 H), 7.10-6.90 (m, 3 H), 4.30-4.15 (m, 5 H), 4.15-4.05 (m, 1 H), 4.05-3.90 (s, 2 H), 1.28 (t, 3 H)

Workup

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

Sources & evidence

ORD record
ord-bddd5ba06d964adc9306de3088a92f1f
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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