Reacción #1308

ord-a7d11788629c4e828999fce2494a1099

Ecuación de reacción

CC(C)(O)CCCc1cccc(Br)c1
5-(3-bromophenyl)-2-methyl-pentan-2-ol
CC(C)(O)CCCc1cccc(Br)c1
Compound E
CC(C)(O)CCCc1cccc(Br)c1
5-(3-bromophenyl)-2-methyl-pentan-2-ol
O=S(=O)(O)O
H2SO4
CC1(C)CCCc2cc(Br)ccc21
title compound
CC1(C)CCCc2cc(Br)ccc21
6-Bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted with Et2O (3×40 ml)
  2. 2
    LavadoThe combined organic layers were washed with water, sat. aqueous NaHCO3 and brine
  3. 3
    Secadodried over MgSO4
  4. 4
    Concentraciónconcentrated in vacuo
  5. 5
    OtroPurification
  6. 6
    workup.DISTILLATIONby kugelrohr distillation

Procedimiento

15.0 g (58.3 mmol) of 5-(3-bromophenyl)-2-methyl-pentan-2-ol (Compound E) was cooled to 0° C. and then 2.8 ml of conc. H2SO4 was added. The mixture was stirred for 2.5 hours, diluted with water (20 ml) and extracted with Et2O (3×40 ml). The combined organic layers were washed with water, sat. aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Purification by kugelrohr distillation gave the title compound as a colorless oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723620uspto-grants-1998_03