Allyl bromide → HCID 14838649, compound

HRID 477489Notes

Reaction equation

HRID 477489 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Product 1

HCID 14838649HCID 14838649, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 4-chloro-2-hydroxybenzoate (2f) (96.3 g, 0.52 mol), allyl bromide (134 ml, 1.55 mol) and ground potassium carbonate (107 g, 0.77 mol) in 1500 ml of dry acetone was heated under reflux for 20 hours. The inorganic salt was removed by filtration, and the solvent and excess allyl bromide evaporated to dryness to give 3f (117 g, 99.6% yield) as a yellow solid, mp 47°-55° C. NMR (CDCl3) δ 7.73 (d, 1H, J=8 Hz, aromatic proton meta to Cl), 6.97 (m, 2H, aromatic protons alpha to Cl), 6.40-5.17 (m, 3H, olefinic protons), 4.57 (m, 2H, CH2) and 3.90 (s, 3H, CH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe inorganic salt was removed by filtration
  4. customthe solvent and excess allyl bromide evaporated to dryness

Sources & evidence

ORD record
ord-7ccd6ca045a7440ab68a080003569b73
Source dataset
uspto-grants-1989_12
Patent number
US04888353

Reaction notes

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