Ethylene Glycol → 2-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one-7-ethylene ketal

HRID 126736Notes

Reaction equation

HRID 126736 reaction equation
[OH:1][CH2:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1.[CH2:17](O)[CH2:18][OH:19].CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:18]1[O:19][C:11]2([CH2:12][CH2:13][CH:14]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3](=[O:16])[CH2:2][OH:1])[O:15][CH2:17]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 202876282-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

Product 1

HCID 867375372-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one-7-ethylene ketal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.5 g. of 2-(8-hydroxy-7-oxo-octyl)cyclopent-2-en-1-one (Example 88), 25 ml. of ethylene glycol, and 0.1 g. of P-toluenesulfonic acid in 200 ml. of toluene is reflucted for 40 minutes using a Dean-Stark trap. The solution is poured into saturated sodium bicarbonate. The mixture is extracted with benzene. The organic solution is washed three times with water and dried over magnesium sulfate. The solvent is removed to give 6.0 g. of the title compound.

Workup

  1. extractionThe mixture is extracted with benzene
  2. washThe organic solution is washed three times with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is removed
  5. customto give 6.0 g

Sources & evidence

ORD record
ord-f49fcb853420467cba341134c29cc80e
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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