Cyclohexanol → 2-Bromobenzyl cyclohexyl ether

HRID 1182380Notes

Reaction equation

HRID 1182380 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Br>CN(C)C=O>[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][O:9][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromide

Product 1

HCID 111732332-Bromobenzyl cyclohexyl etherYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.2 g of sodium hydride at 50% in suspension in oil are added at 5° C., in portions, to 5 g of cyclohexanol in solution in 150 ml of dimethylformamide. The mixture is stirred for 1 hour at room temperature and 12.5 g of 2-bromobenzyl bromide in solution in 15 ml of dimethylformamide are introduced at 5° C. After 2 hours at room temperature, the reaction medium is poured over ice-cold water and extracted with ethyl acetate. The organic phase is dried over anhydrous sodium sulfate and evaporated to give 13.3 g of oil.

Workup

  1. waitAfter 2 hours at room temperature
  2. additionthe reaction medium is poured over ice-cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6b03538b6dbd41919e931e1004f5a61e
Source dataset
uspto-grants-2007_10
Patent number
US07288659B2

Reaction notes

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