Allyl bromide → HCID 25056772, compound

HRID 1258967Notes

Reaction equation

HRID 1258967 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:16]([O:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 118629Ethyl 5-methylsalicylate

Product 1

HCID 25056772HCID 25056772, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 2-hydroxy-5-methyl-benzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 2-Allyloxy-5-methyl-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.52 (s, —CO2H); 7.43 (m, 1 arom. H); 7.26 (m, 1 arom. H); 6.98 (m, 1 arom. H); 5.99 (m, —CH═CH2); 5.46, 5.22 (2 d-like, CH═CH2); 4.56 (d-like, CH2—CH═CH2); 2.23 (s, —CH3). 13C-NMR (100 MHz, d6-DMSO): 167.39 (C═O); 154.91; 133.52; 133.20; 130.91; 129.05; 121.34; 116.83; 113.79; 68.69; 19.78.

Sources & evidence

ORD record
ord-0db4b9382525448eab9573fed36acbfe
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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