Allyl bromide → 2,6,6-Trimethyl-1-(1-hydroxy-3-butenyl)-1-cyclohexene

HRID 1448872Notes

Reaction equation

HRID 1448872 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:13])([CH3:12])[C:7]=1[CH:14]=[O:15].[NH4+].[Cl-]>CCOCC>[CH3:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:12])([CH3:13])[C:7]=1[CH:14]([OH:15])[CH2:3][CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 9895beta-CyclocitralHCID 25517Ammonium Chloride

Product 1

HCID 124203212,6,6-Trimethyl-1-(1-hydroxy-3-butenyl)-1-cyclohexeneYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a typical experiment 10.7 g. of Mg turnings and 5 g. of allyl bromide were allowed to react in 70 ml. of dry ether. The reaction was exothermic and the temperature of the reaction mixture increased up to the boiling point of the solvent. To this solution allyl bromide (46 g.) and β-cyclocitral (61 g.) in 160 ml. of ether were added with vigorous stirring at such a rate as to maintain the ether at the boiling temperature. The reaction mixture was then kept at reflux during 6 hours and after cooling it was poured into a ice-cold concentrated aqueous solution of NH4Cl. The ethereal layer after the usual treatments gave 2,6,6-trimethyl-1-[1-hydroxy-3-butenyl]-1-cyclohexene (44.5 g.; 57% yield): B.p. 60°-2°/0.001 Torr; nD20 =1.4964; d420 =0.9398.

Workup

  1. customto react in 70 ml
  2. temperaturethe temperature of the reaction mixture increased up to the boiling point of the solvent
  3. temperatureat reflux during 6 hours
  4. temperatureafter cooling it

Sources & evidence

ORD record
ord-787ce63787e6486ea1a3dc286cf4014c
Source dataset
uspto-grants-1980_02
Patent number
US04187863

Reaction notes

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