Allyl bromide → HCID 19425361, compound

HRID 2399266Notes

Reaction equation

HRID 2399266 reaction equation
[C:1]([O:12][CH2:13][CH3:14])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[CH2:21]([O:9][C:8]1[CH:10]=[C:2]([CH:3]=[C:4]([O:5][CH2:8][CH:6]=[CH2:4])[C:6]=1[O:7][CH2:3][CH:2]=[CH2:1])[C:1]([O:12][CH2:13][CH3:14])=[O:11])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13250Ethyl gallate

Product 1

HCID 19425361HCID 19425361, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl gallate (7.92 g, commercially available, Fluka), and K2CO3 (27.6 g) in DMF (40 ml) were treated with allyl bromide (13.5 ml) as above, to give ethyl 3,4,5-triallyloxybenzoate acid (14 g): NMR (CDCl3) 1.49 (t, 3H); 4.35 (q, 2H); 4.62 (m, 6H); 5.15-5.48 (m, 6H); 6.00-6.28 (m, 3H); 7.29 (s, 1H). This crude ester was hydrolysed essentially as above to give 3,4,5-triallyloxybenzoic acid (10.4 g): NMR (CDCl3) 4.64 (m, 6H); 5.15-5.51 (m, 6H); 6.00-6.20 (m, 3H); 7.35 (s, 1H).

Sources & evidence

ORD record
ord-7ba8cc7ed23248f9a4536d951b2d7488
Source dataset
uspto-grants-1995_09
Patent number
US05447925

Reaction notes

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