Allyl bromide → HCID 25056770, compound

HRID 1258971Notes

Reaction equation

HRID 1258971 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:14])=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10])(=[O:3])[CH3:2].[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:17][CH:16]=[CH2:15])=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 25056770HCID 25056770, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 5-acetyl-2-hydroxyl-benzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 5-Acetyl-2-allyloxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.94 (s, —CO2H); 8.21 (m, 1 arom. H); 8.06 (m, 1 arom. H); 7.20 (m, 1 arom. H); 6.02 (m, —CH═CH2); 5.50, 5.28 (2 d-like, CH═CH2); 4.73 (d-like, CH2—CH═CH2); 2.53 (s, CH3C═O). 13C-NMR (100 MHz, d6-DMSO): 195.91 (CH3C═O); 166.71 (C(OH)═O); 160.44; 133.22; 132.76; 131.12; 129.11; 121.46; 117.30; 113.35; 69.81; 26.42.

Sources & evidence

ORD record
ord-9ec6d4622e8742fe8b94a0887ca874d8
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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