Cyclohexene oxide → HCID 18653088, compound

HRID 1608480Notes

Reaction equation

HRID 1608480 reaction equation
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1Br)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:17]12[O:23][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2>O1CCCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[OH:23])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 5462224Magnesium

Product 1

HCID 18653088HCID 18653088, compoundYield 69,629.602%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-30 °C

Procedure

A mixture of 3.24 g (0.1 35 mol) of magnesium and 20 ml of tetrahydrofuran was charged into a three-necked flask of 300 ml and stirred. Then, a solution of 35.6 g of o-benzyloxyphenylbromide in 80 ml of tetrahydrofuran was added dropwise at a temperature of 60° C. or less. After the dropping was stopped, the mixture was cooled to -30° C., 0.65 g of cuprous chloride was added, and the mixture was stirred for 10 minutes. To the mixture, a solution of 13.3 g (0.135 mol ) of cyclohexene oxide in 15 ml tetrahydrofuran was added dropwise at -30° C. After the dropping was stopped. The temperature was raised to 0° C., and the mixture was stirred for three hours at 0° C. After the temperature was raised to room temperature, the mixture was charged into a separatory funnel and extracted with 600 ml of methylene chloride, and the organic layer was washed with 600 ml of saturated ammonium sulfate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled away under reduced pressure. The concentrate was distilled under reduced pressure to obtain 26.5 g (0,094 mol) of (±)-trans-2-(2-benzyloxyphenyl)-1-cyclohexanol.

Workup

  1. additionwas charged into a three-necked flask of 300 ml
  2. stirringthe mixture was stirred for 10 minutes
  3. temperatureThe temperature was raised to 0° C.
  4. stirringthe mixture was stirred for three hours at 0° C
  5. temperatureAfter the temperature was raised to room temperature
  6. additionthe mixture was charged into a separatory funnel
  7. extractionextracted with 600 ml of methylene chloride
  8. washthe organic layer was washed with 600 ml of saturated ammonium sulfate
  9. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled away under reduced pressure
  11. distillationThe concentrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-9c793fad0960452682279bdfd6ab1b16
Source dataset
uspto-grants-1995_03
Patent number
US05395766

Reaction notes

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