2-Methoxypropene → Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-

HRID 893763Notes

Reaction equation

HRID 893763 reaction equation
CO[C:3]([CH3:5])=[CH2:4].[Br:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH2:17][OH:18])[CH:11]=1)=[O:9]>C(Cl)Cl>[Br:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][C:3]([CH3:5])([CH3:4])[O:18][CH2:17][C:12]=2[CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 83002-MethoxypropeneHCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-one

Product 1

HCID 11150315Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-Yield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxypropene (10 g) was added over 15 min to a stirred solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (5 g) and toluene-4-sulfphonic acid (0.5 g) in CH2Cl2 (100 ml) at 23° C. The mixture was stirred for 3 h, filtered through a wad of triemethylamine-deactivated silica and evaporated to give an oil. Purification by [FCTS] (300 g) [E] afforded the title compound as an oil (4.8 g) which solidified on cooling. A small sample was crystallized from light petroleum (b.p. 60°-80°) to give white crystals m.p. 47°-48°.

Workup

  1. filtrationfiltered through a wad of triemethylamine-deactivated silica
  2. customevaporated
  3. customto give an oil
  4. customPurification by [FCTS] (300 g) [E]

Sources & evidence

ORD record
ord-c38194f1e76044ec96aa57da9b77ee2b
Source dataset
uspto-grants-1992_06
Patent number
US05126375

Reaction notes

Loading…