Ethyl Bromide → HCID 178448088, compound

HRID 1730613Notes

Reaction equation

HRID 1730613 reaction equation
[H-].[Na+].[C:3]([C@@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)([CH3:5])=[CH2:4].[CH2:14](Br)[CH3:15]>CS(C)=O>[CH2:14]([O:13][CH2:12][C@H:9]1[CH2:10][CH2:11][C@@H:6]([C:3]([CH3:5])=[CH2:4])[CH2:7][CH2:8]1)[CH3:15]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 178448083HCID 178448083, compound

Product 1

HCID 178448088HCID 178448088, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6 g of sodium hydride -- 50% in mineral oil -- were allowed to react with 100 ml of dimethyl-sulfoxide, at 55° - 60° for 90 min. 7.5 g of cis-4-isopropenyl-cyclohexylmethanol were then added to the resulting solution, followed by a dropwise addition of 20 g of ethyl bromide. The reaction mixture was stirred overnight at room temperature, then poured onto crushed ice and finally extracted with hexane. After the usual treatments of washing, drying and evaporation, the fractional distillation of the obtained residue yielded cis-4-isopropenyl-cyclohexylmethyl ethyl ether, bp 96° - 97°/10 Torr.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionfinally extracted with hexane
  4. washAfter the usual treatments of washing
  5. customdrying
  6. customevaporation
  7. distillationthe fractional distillation of the obtained residue

Sources & evidence

ORD record
ord-c457688303f540e7b369444451b00d9c
Source dataset
uspto-grants-1976_11
Patent number
US03993604

Reaction notes

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