Ethylparaben → 4-(3-methylbut-2-enoxy)benzoic acid

HRID 1258963Notes

Reaction equation

HRID 1258963 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.[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16][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 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 2671374-(3-methylbut-2-enoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 4-hydroxybenzoate and 3,3-dimethylallyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 4-(3-Methyl-but-2-enyloxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.54 (s, —CO2H); 7.81 (d-like, 2 arom.H); 6.95 (d-like, 2 arom.H); 5.38 (m, CH═C(CH3)2); 4.54 (d-like, CH2CH═C(CH3)2); 1.69, 1.64 (2s, CH═C(CH3)2). 13C-NMR (100 MHz, d6-DMSO): 166.96 (C═O); 162.05; 137.66; 131.25 (2 arom. C); 122.78; 119.38; 114.36 (2 arom.C); 64.58; 25.37; 17.99.

Sources & evidence

ORD record
ord-0a290677b6914303b9ae876ab031d410
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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