Allyl bromide → HCID 14838643, compound

HRID 477484Notes

Reaction equation

HRID 477484 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:12][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[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 14838643HCID 14838643, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 5-chloro-2-hydroxybenzoate (2c) (45.0 g, 0.24 mol), allyl bromide (62.6 ml, 0.75 mol) and ground potassium carbonate (66.67 g, 0.48 mol) in 750 ml of dry acetone was heated under reflux for 21/2 hours. The inorganic salt was removed by filtration, and the solvent and excess allyl bromide in the filtrate was evaporated to dryness to yield compound 3c quantitatively as a white solid, mp 25°-26° C. IR (nujol) 1738 (ester) cm-1. NMR (CDCl3) δ 7.63 (d, 1H, JBC =3 Hz, HC), 7.27 (d of d, 1H, JAB =9 Hz, HB), 6.77 (d. 1H, HA), 6.30-6.47 (m, 3H, olefinic protons) and 3.87 (s, 3H, CH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21/2 hours
  3. customThe inorganic salt was removed by filtration
  4. customthe solvent and excess allyl bromide in the filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-47c4d2061670486e899de414dc10372a
Source dataset
uspto-grants-1989_12
Patent number
US04888353

Reaction notes

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