Allyl bromide → HCID 12403852, compound

HRID 849062Notes

Reaction equation

HRID 849062 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[C:7]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(Br)C=C>C1C=CC=CC=1.OS([O-])(=O)=O.[K+].CCOCC.O>[CH2:3]([CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:7]1=[O:14])[CH:2]=[CH2:1]

Participants

8

Reactant 3

HCID 7841Allyl bromideHCID 10400CycloheptanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 12403852HCID 12403852, compoundYield 32.1%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516920Potassium bisulfateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mechanically stirred mixture of potassium t-butoxide (Aldrich, 67.0 g, 0.6 mol) in benzene (600 mL) cooled to 0° C. under a nitrogen atmosphere was added cycloheptanone (Aldrich, 56.1 g, 0.5 mol) dropwise over 15 minutes. Ten minutes after the addition was complete, allyl bromide (Aldrich, 61.6 g, 0.51 mol) was added dropwise over 20 minutes. The reaction was warmed to room temperature, refluxed or 7 hrs., stirred at room temperature for 18 hrs., and diluted with 0.5 N KHSO4 (300 mL). This mixture was further diluted with Et2O (600 mL), 3.5 N KHSO4 (200 mL) and H2O (200 mL) before the organic was separated, washed with H2O (200 mL) and brine (200 mL), dried (Na2SO4), filtered, and stripped of all solvent under reduced pressure. The crude product (76.1 g) was distilled to yield 24.4 g (32%) of the title material (bp=104-108° C., 25 mm of Hg).

Workup

  1. additionTen minutes after the addition
  2. temperatureThe reaction was warmed to room temperature
  3. temperaturerefluxed or 7 hrs
  4. customorganic was separated
  5. washwashed with H2O (200 mL) and brine (200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. distillationThe crude product (76.1 g) was distilled

Sources & evidence

ORD record
ord-974d5823dee24a29b40f4b588f5f6abc
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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