Hydrogen Bromide → HCID 54298637, compound

HRID 1284178Notes

Reaction equation

HRID 1284178 reaction equation
[BrH:1].[CH:2]1([C:5](O)([CH2:7][CH2:8][O:9][CH:10]([CH3:12])[CH3:11])[CH3:6])[CH2:4][CH2:3]1>>[Br:1][CH2:4][CH2:3][CH:2]=[C:5]([CH3:6])[CH2:7][CH2:8][O:9][CH:10]([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 21515717HCID 21515717, compound

Product 1

HCID 54298637HCID 54298637, compound

Procedure

19 cc of 48 % hydrobromic acid are added dropwise, whilst stirring, at 0°C, over the course of 15 minutes, to 27.7 g of crude 2-cyclopropyl-4-isopropoxy-2-butanol. The mixture is stirred at 0°-5°C over the source of 30 minutes, and subsequently extracted with ether. The ether extract is washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulphate and evaporated. The residue (20.2 g) is chromatographed with hexane/ethyl acetate (98:2) and (95:5) on silica gel. A chromatographically pure cis, trans isomeric mixture of 1-bromo-6-isopropoxy-4-methyl-3-hexene is obtained, nD20 = 1.4802.

Workup

  1. extractionsubsequently extracted with ether
  2. extractionThe ether extract
  3. washis washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue (20.2 g) is chromatographed with hexane/ethyl acetate (98:2) and (95:5) on silica gel
  7. additionA chromatographically pure cis, trans isomeric mixture of 1-bromo-6-isopropoxy-4-methyl-3-hexene
  8. customis obtained

Sources & evidence

ORD record
ord-c4bb4be38885461c98e8d5932dca6d93
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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