Water → ((Cyclohex-2-enyloxy)methyl)benzene

HRID 527013Notes

Reaction equation

HRID 527013 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[H-].[Na+].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1COCC1.CCOCC>[CH:1]1([O:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 131982-Cyclohexen-1-OLHCID 24758Sodium hydride

Product 1

HCID 10867111((Cyclohex-2-enyloxy)methyl)benzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of cyclohex-2-en-1-ol (10.0 g, 101.9 mmol) in anhydrous THF (100 mL) was added to a stirred suspension containing sodium hydride (8.0 g, 199.7 mmol) (60% dispersion in oil) and benzyl bromide in anhydrous THF (250 mL) maintained at 50° C. The resulting solution was stirred at 55-60° C. for 18 h. After cooling to ambient temperature, water was added to quench the reaction and the mixture was diluted with ether (500 mL). The organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo to an oil that was subjected to a short silica plug filtration to provide 16.1 g of desired product 51a that was used directly in the next step without further purification.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customto quench
  3. customthe reaction
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an oil that
  8. filtrationwas subjected to a short silica plug filtration

Sources & evidence

ORD record
ord-b10b40a6bab840a290a8c20455a598f0
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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