Allyl bromide → alpha-Allylbenzoin methyl ether

HRID 279905

Reaction equation

HRID 279905 reaction equation
[CH3:1][O:2][CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:18][C:19](C)([O-])[CH3:20].[K+].C(Br)C=C>C(O)(C)(C)C>[CH3:1][O:2][C:3]([CH2:20][CH:19]=[CH2:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 98097Methyl BenzoinHCID 23665647Potassium tert-butoxide

Product 1

HCID 20441990alpha-Allylbenzoin methyl etherYield 83.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Benzoin methyl ether (50 g) and t-butanol (500 g) were added to a 1 liter, 3-neck round bottom flask equipped with magnetic stirrer, and placed in an oil bath at 80° C. To this mixture, 33.7 g of potassium t-butoxide was added and the solution stirred for 15 minutes. Allyl bromide (42.3 g) was added dropwise over a 1 hour period and stirring was continued at 85° C. for 2 more hours followed by cooling to room temperature. After evaporation of t-butanol and filtration of potassium bromide, the product was distilled at 125° C.±2° C. and 0.05 mm Hg to yield 49.2 g of α-allylbenzoin methyl ether which crystallized upon cooling.

Workup

  1. customequipped with magnetic stirrer
  2. customplaced in an oil bath at 80° C
  3. stirringstirring
  4. customwas continued at 85° C. for 2 more hours
  5. customAfter evaporation of t-butanol and filtration of potassium bromide
  6. distillationthe product was distilled at 125° C.±2° C.

Sources & evidence

ORD record
ord-4b74e43a74af4b369025d24061fc87ed
Source dataset
uspto-grants-1986_05
Patent number
US04587276

Linked notes

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