Water → Ethyl 4-(4-acetyl-2-methoxyphenoxy)butanoate

HRID 1797829Notes

Reaction equation

HRID 1797829 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br)[CH3:20].O>CN(C)C=O>[C:2]([C:4]1[CH:12]=[CH:11][C:9]([O:10][CH2:25][CH2:24][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:27])=[C:6]([O:7][CH3:8])[CH:5]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 2214AcetovanilloneHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 60562321Ethyl 4-(4-acetyl-2-methoxyphenoxy)butanoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. stirringstirred for 24 h
  2. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-8c61c6aaf4e0493092280eee0e58b37d
Source dataset
uspto-grants-2013_01
Patent number
US08343710B1

Reaction notes

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