Diethyl Ether → 1-[3-(1-Ethoxyethoxy)propyl]cyclohex-2-en-1-ol

HRID 1980403Notes

Reaction equation

HRID 1980403 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Cl-].[NH4+].[CH:10]1([OH:16])[CH2:15][CH2:14]CC=C1.[CH2:17]([O:19][CH2:20][CH3:21])[CH3:18]>>[CH2:17]([O:19][CH:20]([O:16][CH2:10][CH2:15][CH2:14][C:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)[CH3:21])[CH3:18]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 131982-Cyclohexen-1-OLHCID 135942-Cyclohexen-1-one2×HCID 25517Ammonium Chloride

Product 1

HCID 204028901-[3-(1-Ethoxyethoxy)propyl]cyclohex-2-en-1-ol

Conditions

Temperature
0 °C

Procedure

The organo-lithium intermediate compound formed in this above reaction mixture was transferred via a cannulus apparatus to a 250 ml oven dried, round bottom flask fitted with magnetic stir bar, septum, pressure equalizing additional funnel connected to a source of nitrogen and cooled to 0° C. in an ice/water bath. The addition funnel had been charged with 9.95 g (0.10 mol) of 2-cyclohexen-1-one and 100 ml of anhydrous ethyl ether. The cyclohexenone solution was added dropwise to the cold, stirred organolithium intermediate compound under nitrogen over a 1.5 hr period. The resultant mixture was stirred at 0° C. for one hr and then allowed to slowly warm to room temperature by stirring for 18 hr without replenishing the ice in the bath. The reaction mixture was poured into 250 ml of ice cold, 1/2 saturated ammonium chloride aqueous solution. The liquid phases were separated and the aqueous phase was extracted twice with 200 ml portions of diethyl ether. The combined ethereal liquid phases were washed with brine solution, dried over sodium sulfate and concentrated in vacuo to leave 21.4 g (93% yield) of the above named -cyclohex-2-ene-1-ol intermediate as a colorless oil which was used as such in the next step. The NMR of this intermediate was consistent with the above named intermediate compound.

Workup

  1. customabove reaction mixture
  2. customwas transferred via a cannulus apparatus to a 250 ml oven
  3. customdried
  4. customround bottom flask fitted with magnetic stir bar
  5. temperatureto slowly warm to room temperature
  6. customThe liquid phases were separated
  7. extractionthe aqueous phase was extracted twice with 200 ml portions of diethyl ether
  8. washThe combined ethereal liquid phases were washed with brine solution
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto leave 21.4 g (93% yield) of the

Sources & evidence

ORD record
ord-39bce0002fe84b978df64df1ca3a6f32
Source dataset
uspto-grants-1985_04
Patent number
US04508911

Reaction notes

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