Allyl bromide → 4-(Prop-2-en-1-yloxy)benzoic acid

HRID 1258956Notes

Reaction equation

HRID 1258956 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.[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 4606904-(Prop-2-en-1-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 4-hydroxybenzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 4-Allyloxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.56 (s, —CO2H); 7.83 (d-like, J=8.0, 2 arom. H); 6.97 (d-like, J=8.0, 2 arom. H); 5.99 (m, —CH═CH2); 5.38, 5.24 (2 d-like, —CH═CH2); 4.59 (d-like, CH2—CH═CH2); 13C-NMR (100 MHz, d6-DMSO): 166.92 (—C═O); 161.72; 133.17; 131.28 (2 arom. C); 123.04; 117.80; 114.42 (2 arom. C); 68.34.

Sources & evidence

ORD record
ord-053be521f47c44c1b89637728c319c0a
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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