Ethyl Salicylate → HCID 15194782, compound

HRID 1258957Notes

Reaction equation

HRID 1258957 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].Br[CH2:14][CH2:15][CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:17]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])[CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 8365Ethyl SalicylateHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 15194782HCID 15194782, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl salicylate and 4-bromo-1-butene in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 2-But-3-enyloxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.57 (s, —CO2H); 7.63 (m, 1 arom. H); 7.46 (m, 1 arom. H); 7.12 (m, 1 arom. H); 6.99 (m, 1 arom. H); 5.92 (m, —CH═CH2); 5.18, 5.08 (2 d-like, —CH═CH2); 4.07 (t, J=6.4, OCH2—CH2—CH═CH2); 2.49 (m, OCH2—CH2—CH═CH2). 13C-NMR (100 MHz, d6-DMSO): 167.33 (—C═O); 157.18; 134.77; 132.85; 130.52; 121.75; 120.16; 117.01; 113.60; 67.70; 33.20.

Sources & evidence

ORD record
ord-85844c700352460b941b4f5b840ba94b
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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