Acetic Acid → 5,5-Diphenyl-4-pentenyl bromide

HRID 851302Notes

Reaction equation

HRID 851302 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(O)[CH2:8][CH2:9][CH2:10][CH2:11]OC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[BrH:25]>O>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH2:9][CH2:10][CH2:11][Br:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 131250861,1-Diphenyl-5-methoxy-1-pentanol

Product 1

HCID 155508755,5-Diphenyl-4-pentenyl bromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the pentanol prepared as above (8.88 g., 0.0328 mole) in 132 ml. of glacial acetic acid and 66 ml. of distilled hydrobromic acid was stirred at ambient temperature for two hours and then refluxed for 90 minutes. The reaction mixture was cooled, diluted with water and extracted with ether. The ether extract was washed with 5% sodium carbonate solution, water, dried and concentrated to obtain an oil which is chromatographed on silica to yield 5,5-diphenyl-4-pentenyl bromide.

Workup

  1. temperaturerefluxed for 90 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with 5% sodium carbonate solution, water
  6. customdried
  7. concentrationconcentrated
  8. customto obtain an oil which
  9. customis chromatographed on silica

Sources & evidence

ORD record
ord-b2d565f5a9504146902b89bcef5d607a
Source dataset
uspto-grants-1983_05
Patent number
US04383999

Reaction notes

Loading…