Diethyl Ether → HCID 53660533, compound

HRID 981013Notes

Reaction equation

HRID 981013 reaction equation
[CH2:1]([O:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][OH:19])[CH2:2][CH2:3][CH2:4][CH3:5].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C(OCC)C>ClCCl>[CH2:1]([O:6][CH:7]1[C:18](=[O:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 54163183HCID 54163183, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53660533HCID 53660533, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.8 g of diatomaceous earth and a solution of 5.39 g of 12-pentyloxy-4,8-dodecadien-1-ol in 50 ml of dichloromethane were charged into a 250 ml flask. 8.8 g of PCC were then added in small portions and the mixture was stirred for 2 h at room temperature. Ethyl ether was added to the reaction mixture to precipitate the chromium salts, and the mixture was then filtered on SiO2, concentrated and distilled in a bulb-to-bulb apparatus. 4 g of 12-pentyloxy-4,8-cyclododecadien-1-one were obtained.

Workup

  1. customto precipitate the chromium salts
  2. filtrationthe mixture was then filtered on SiO2
  3. concentrationconcentrated
  4. distillationdistilled in a bulb-to-bulb apparatus

Sources & evidence

ORD record
ord-02f13e556c064a049b6f76c89a988076
Source dataset
uspto-grants-1991_02
Patent number
US04990495

Reaction notes

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