2-Bromopropane → HCID 68481940, compound

HRID 1873456Notes

Reaction equation

HRID 1873456 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][C:3]1([C:11]([CH3:13])=[CH2:12])[CH:9]=[O:10].Br[CH:15]([CH3:17])[CH3:16]>>[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][C:3]1([CH:9]([OH:10])[CH:15]([CH3:17])[CH3:16])[C:11]([CH3:13])=[CH2:12]

Participants

3

Reactant 2

HCID 63582-BromopropaneHCID 59440844HCID 59440844, compound

Product 1

HCID 68481940HCID 68481940, compoundYield 72%

Procedure

To a mixture of Mg (1.2 g, 50 mmol), Li (0.35 g, 50 mmol) and 2,4-dimethyl-1-(prop-1-en-2-yl)cyclohex-3-enecarbaldehyde (8.9 g, 50 mmol) was added 2-bromopropane (7.5 g, 60 mmol). The mixture was stirred for 24 h under an argon atmosphere and was then poured on ice-cold sat. NH4Cl solution. The mixture was extracted with MTBE (3×50 ml). The combined org. phases were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled in a Kugelrohr oven to yield 8.0 g (72%) of a colorless oil.

Workup

  1. additionwas then poured on ice-cold sat. NH4Cl solution
  2. extractionThe mixture was extracted with MTBE (3×50 ml)
  3. washphases were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was distilled in a Kugelrohr oven

Sources & evidence

ORD record
ord-ba8a9e5b742d45f1bf9dda95ba172b1f
Source dataset
uspto-grants-2012_11
Patent number
US08304380B2

Reaction notes

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