Benzyl Bromide → HCID 20334277, compound

HRID 1706717Notes

Reaction equation

HRID 1706717 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:17])[CH2:7][C:8]([CH3:16])([CH2:13][CH2:14][CH3:15])[O:9]2)=[CH:4][CH:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:18]([O:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:17])[CH2:7][C:8]([CH3:16])([CH2:13][CH2:14][CH3:15])[O:9]2)=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 20334274HCID 20334274, compound

Product 1

HCID 20334277HCID 20334277, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 11.7 g. of the compound obtained in (1), 11.1 g. of benzyl bromide, 10.2 g. of potassium carbonate, and 100 ml of acetone was refluxed for 2 hours, followed by filtration. The filtrate was concentrated. Ether was added to the concentrate. The ether solution was washed successively with water, 1 N aqueous solution of sodium hydroxide, and again with water, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by subjecting to column chromatography filled with silica gel, to obtain 11.5 g. (yield: 91.0%) of the subject compound. Melting point: 45° C.

Workup

  1. additionThe mixture of 11.7 g
  2. filtrationfollowed by filtration
  3. concentrationThe filtrate was concentrated
  4. additionEther was added to the concentrate
  5. washThe ether solution was washed successively with water, 1 N aqueous solution of sodium hydroxide
  6. dry with materialagain with water, and then dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified
  9. additionfilled with silica gel
  10. customto obtain 11.5 g

Sources & evidence

ORD record
ord-20c152c2317043eb96449a9b7c564790
Source dataset
uspto-grants-1980_06
Patent number
US04208426

Reaction notes

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