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

HRID 709324Notes

Reaction equation

HRID 709324 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-b03d11d8ece0409ba1470e638d7e22c1
Source dataset
uspto-grants-2015_11
Patent number
US09180196B2

Reaction notes

Loading…