Ethylparaben → 4-[(2-Methylprop-2-en-1-yl)oxy]benzoic acid

HRID 1258974Notes

Reaction equation

HRID 1258974 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][C:15]([CH3:17])=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:16][C:15](=[CH2:14])[CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 159433014-[(2-Methylprop-2-en-1-yl)oxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of Ethyl 4-hydroxyl-benzoate and 3-Bromo-2-methyl-propene in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 4-(2-Methyl-allyloxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO):12.59 (s, —CO2H); 7.86 (d-like, J=8.0, 2 arom. H); 7.02 (d-like, J=8.0, 2 arom. H); 5.04, 4.96 (2 s, —C(CH3)═CH2); 4.53 (s, CH2—C(CH3)═CH2); 1.72 (s, C(CH3)═CH2). 13C-NMR (100 MHz, d6-DMSO): 166.93 (—C═O); 161.87; 140.39; 131.27 (2 arom. C); 123.05; 114.42 (2 arom. C); 112.52; 70.97; 19.12.

Sources & evidence

ORD record
ord-ebad3b10665d41fb8e09bdb669589159
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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