Ethylparaben → 4-(3-Butenyloxy)benzoic acid

HRID 1258958Notes

Reaction equation

HRID 1258958 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][CH2:15][CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)[CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 5444524-(3-Butenyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 4-hydroxybenzoate and 4-bromo-1-butene in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 4-But-3-enyloxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.57 (s, —CO2H); 7.89 (d, J=6.9, 2 arom. H); 7.00 (d, J=6.9, 2 arom. H); 5.86 (m, —CH═CH2); 5.19, 5.08 (2 d-like, CH═CH2); 4.00 (t, J=6.6, OCH2—CH2—CH═CH2); 2.50 (m, OCH2—CH2—CH═CH2). 13C-NMR (100 MHz, d6-DMSO): 166.95 (—C═O); 162.08; 134.66; 131.32 (2 arom. C); 122.92; 117.14; 114.22 (2 arom. C); 66.92; 32.90.

Sources & evidence

ORD record
ord-e848f23caec6495aa6150972371fe4f9
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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