Potassium Carbonate → HCID 59290097, compound

HRID 1258959Notes

Reaction equation

HRID 1258959 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[O:6].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]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[O:6])[CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 59290097HCID 59290097, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 3-hydroxybenzoate and 4-bromo-1-butene in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 3-But-3-enyloxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.96 (s, —CO2H); 7.48 (d-like, 1 arom. H); 7.40 (m, 2 arom. H); 7.18 (m, 1 arom. H); 5.86 (m, —CH═CH2); 5.15, 5.08 (2 d-like, CH═CH2); 4.03 (t, J=6.6, OCH2—CH2—CH2═CH2); 2.47 (m, OCH2—CH2—CH═CH2). 13C-NMR (100 MHz, d6-DMSO): 167.07 (—C═O); 158.44; 134.79; 132.18; 129.70; 121.55; 119.31; 117.04; 114.54; 66.84; 32.90.

Sources & evidence

ORD record
ord-d31ac4fcb2d94367b6b965ad5d442078
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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