Water → 6,6-Dimethylhept-2-en-4-yn-1-ol

HRID 580004Notes

Reaction equation

HRID 580004 reaction equation
Br[CH2:2][CH:3]=[CH:4][C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-:12].[Na+].[Na+].O>CC(C)=O>[CH3:8][C:7]([CH3:10])([CH3:9])[C:6]#[C:5][CH:4]=[CH:3][CH2:2][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 534004696,6-Dimethylhept-2-en-4-yn-1-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 5.24 g (26.0 mmol) of an approximately 3:1 mixture of the E and Z isomers of 1-bromo-6,6-dimethyl-2-hepten-4-yne was added sodium carbonate (5.52 g, 52.0 mmol) 80 ml of acetone and 170 ml of water. This mixture was heated to reflux for 3 hours. After cooling, most of the acetone was removed in vacuo and the mixture was extracted with ethyl ether three times. The combined ether layer was dried with sodium sulfate and concentrated to afford 3.97 of 6,6-dimethyl-2-hepten-4-yn-1-ol.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 3 hours
  3. customwas removed in vacuo
  4. extractionthe mixture was extracted with ethyl ether three times
  5. dry with materialThe combined ether layer was dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9665406478be47d48fb0242fb7528c8e
Source dataset
uspto-grants-1988_06
Patent number
US04751245

Reaction notes

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