Ethyl Salicylate → HCID 17765538, compound

HRID 1258961Notes

Reaction equation

HRID 1258961 reaction equation
[C:1]([O:10]CC)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[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:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 8365Ethyl SalicylateHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 17765538HCID 17765538, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl salicylate and 3,3-dimethylallyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 2-(3-Methyl-but-2-enyloxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.50 (s, —CO2H); 7.55 (m, 1 arom. H); 7.41 (m, 1 arom. H); 7.07 (m, 1 arom. H); 6.92 (m, 1 arom. H); 5.36 (m, CH═C(CH3)2); 4.54 (d-like, CH2CH═C(CH3)2); 1.72, 1.68 (2s, CH═C(CH3)2). 13C-NMR (100 MHz, d6-DMSO): 167.42 (C═O); 157.06; 136.97; 132.70; 130.44; 121.91; 119.99; 119.82; 113.79; 65.23; 25.42; 18.03.

Sources & evidence

ORD record
ord-c3f2bae2e5dd4e34881bfc9a064062da
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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