Allyl bromide → HCID 54214209, compound

HRID 580969Notes

Reaction equation

HRID 580969 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=1.[Br-].[K+]>CC(C)=O>[CH2:7]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][OH:21])=[CH:16][CH:17]=1)[CH:8]=[CH2:9]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 824523-(4-Hydroxyphenyl)propanolHCID 253877Potassium Bromide

Product 1

HCID 54214209HCID 54214209, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Powdered potassium carbonate (4.14 g) and allyl bromide (3.99 g) were added to a stirred solution of 3-(4-hydroxyphenyl)propanol (4.56 g) in acetone (15 ml) under an atmosphere of argon. The mixture heated at reflux for 20 hours. After cooling to ambient temperature the solid potassium bromide was removed by filtration and washed with ether. The filtrate and washings were combined, washed with 2M aqueous sodium hydroxide (2×20 ml), water (1×20 ml), brine (20 ml), dried (MgSO4) and evaporated. The residue was purified by vacuum flash chromatography on silica gel (Merck 7736) using toluene as eluent to give 3-(4-allyloxyphenyl) propanol as a colourless oil (4.6 g). NMR(CDCl3): 1.3(1H,s), 1.8-2.0(2H,m), 2.6-2.7(2H,t), 3.6-3.7(2H,t), 4.45-4.55(2H,m), 5.2-5.5(2H,m), 5.95-6.15(1H,m), 6.8-6.9(2H,d) and 7.05-7.15(2H,d).

Workup

  1. temperatureThe mixture heated
  2. temperatureat reflux for 20 hours
  3. customwas removed by filtration
  4. washwashed with ether
  5. washwashed with 2M aqueous sodium hydroxide (2×20 ml), water (1×20 ml), brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by vacuum flash chromatography on silica gel (Merck 7736)

Sources & evidence

ORD record
ord-12299a4b427b40c0869530fbda5f229f
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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