Water → 4,4-Ethylenedioxy-4-phenylbutyl bromide

HRID 1607402

Reaction equation

HRID 1607402 reaction equation
[CH2:1]1[CH2:15][O:14][C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH2:4][CH2:5][CH2:6]O)[O:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.C([Br:31])C=C.O>C(#N)C>[CH2:1]1[CH2:15][O:14][C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH2:4][CH2:5][CH2:6][Br:31])[O:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 682631,1'-CarbonyldiimidazoleHCID 223445572-(3-Hydroxypropyl)-2-phenyl-1,3-dioxolane

Product 1

HCID 147642024,4-Ethylenedioxy-4-phenylbutyl bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.2 g of the alcohol compound obtained in 20 ml of acetonitrile were added 1.2 g of 1,1'-carbonyldiimidazole and 2.5 ml of allyl bromide. The mixture was stirred for 2 hours at room temperature and then heated under reflux for 1.5 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1.1 g of 4,4-ethylenedioxy-4-phenylbutyl bromide as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44c9fd90b9fb4f039d1e3e3c147dc398
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Linked notes

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