Reaction #1885011

ord-8c61c6aaf4e0493092280eee0e58b37d

Reaction equation

O
water
COc1cc(C(C)=O)ccc1O
Acetovanillone
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)CCCBr
ethyl-4-bromobutyrate
→
CCOC(=O)CCCOc1ccc(C(C)=O)cc1OC
ethyl 4-(4-ethanoyl-2-methoxyphenoxy)butanoate
Yield 98.1%

Reactants

O
water
COc1cc(C(C)=O)ccc1O
Acetovanillone
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)CCCBr
ethyl-4-bromobutyrate

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGstirred for 24 h
  2. 2
    OtherThe product was isolated by filtration

Procedure

Acetovanillone (16.6 g, 0.10 mol), potassium carbonate (30.0 g, 0.22 mol) and ethyl-4-bromobutyrate (17 mL, 0.12 mol) were combined in dimethylformamide (50 mL) and stirred under Argon for 17.5 h. The reaction was poured into water (800 mL) and stirred for 24 h. The product was isolated by filtration to yield ethyl 4-(4-ethanoyl-2-methoxyphenoxy)butanoate (27.5 g, 98%) as a white powder. 1H NMR (δ, ppm): 1.28 (t, CO2CH2CH3), 2.21 (p, ArOCH2CH2CH2), 2.56 (t, ArOCH2CH2CH2), 2.60 (s, ArCOCH3), 3.92 (s, ArOCH3), 4.13 (t, ArOCH2), 4.18 (q, CO2CH2), 6.92 (d, aromatic H ortho to ArOCH2), 7.54 (s, aromatic H ortho to ArOCH3), 7.58 (d, aromatic H ortho to ArCOCH3).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08343710B1uspto-grants-2013_01