Allyl bromide → 2-Allyloxy-m-anisic acid

HRID 1258966Notes

Reaction equation

HRID 1258966 reaction equation
[OH:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[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[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 80651Methyl 3-methoxysalicylate

Product 1

HCID 30246032-Allyloxy-m-anisic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 2-hydroxy-3-methoxy-benzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 2-Allyloxy-3-methoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.18 (s, —CO2H); 7.10 (m, 3 arom. H); 5.97 (m, —CH═CH2); 5.28, 5.14 (2 d-like, CH═CH2); 4.43 (d-like, CH2—CH═CH2); 3.77 (s, OCH3). 13C-NMR (100 MHz, d6-DMSO): 167.42 (C═O); 153.06; 146.24; 134.49; 127.66; 123.94; 121.07; 117.10; 115.57; 73.88; 55.93.

Sources & evidence

ORD record
ord-f2e414b595464d9ea16a63ff249a1a7d
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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