Allyl bromide → HCID 25056771, compound

HRID 1258970Notes

Reaction equation

HRID 1258970 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][OH:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:18]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][OH:15])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5])[CH:17]=[CH2:16]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 586358Methyl 4-(2-hydroxyethoxy)salicylate

Product 1

HCID 25056771HCID 25056771, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 2-hydroxy-4-(2-hydroxy-ethoxy)-benzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 2-Allyloxy-4-(2-hydroxy-ethoxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.12 (s, —CO2H); 7.65 (d, J=8.7, 1 arom. H); 6.55 (m, 2 arom. H); 5.97 (m, —CH═CH2); 5.48, 5.21 (2 d-like, CH═CH2); 4.84 (m, CH2CH2OH); 4.58 (d-like, CH2—CH═CH2); 3.99, 3.67 (2t, J=4.8, CH2CH2OH). 13C-NMR (100 MHz, d6-DMSO): 166.45 (C═O); 162.93; 159.39; 133.30; 133.24; 116.86; 112.86; 105.84; 100.43; 69.82; 68.58; 59.40.

Sources & evidence

ORD record
ord-6e5850da96094992b2da65b582b46e5d
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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