Allyl bromide → 2-Allyloxy-5-chloro-benzoic acid

HRID 1258973Notes

Reaction equation

HRID 1258973 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:15]([O:12][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 18438862-Allyloxy-5-chloro-benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 5-chloro-2-hydroxyl-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-chloro-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.96 (s, —CO2H); 7.61 (m, 1 arom. H); 7.52 (m, 1 arom. H); 7.12 (m, 1 arom. H); 5.99 (m, —CH═CH2); 5.47, 5.23 (2 d-like, CH═CH2); 4.62 (d-like, CH2—CH═CH2). 13C-NMR (100 MHz, d6-DMSO): 166.08 (C═O); 155.70; 133.02; 132.25; 129.84; 123.85; 123.36; 117.15; 115.70; 68.91.

Sources & evidence

ORD record
ord-df972db762ea4eefbf5aff5cfa8586dd
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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