Benzyl Chloride → HCID 14421497, compound

HRID 1722352Notes

Reaction equation

HRID 1722352 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]=1[OH:15])[CH:2]=[CH2:3].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14421495HCID 14421495, compound

Product 1

HCID 14421497HCID 14421497, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

90 g (0.44 mol) of 2-allyl-6-cyclopentylphenol, 62 g (0.49 mol) of benzyl chloride and 124 g (0.9 mol) of potassium carbonate are heated under reflux in 800 ml of acetone for 70 h. The cooled reaction mixture is filtered, and the filtrate is concentrated. The residue is taken up in petroleum ether, and the solution is washed three times with 2N sodium hydroxide solution and then once each with water and saturated brine. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is distilled in vacuo. 118 g (92% of theory) of 1-allyl-2-benzyloxy-3-cyclopentylbenzene are obtained.

Workup

  1. customThe cooled reaction mixture
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated
  4. washthe solution is washed three times with 2N sodium hydroxide solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationThe residue is distilled in vacuo

Sources & evidence

ORD record
ord-fa2e6de974884a09a12d7dd67c4afba4
Source dataset
uspto-grants-1989_08
Patent number
US04855323

Reaction notes

Loading…