Acetic Anhydride → HCID 20465612, compound

HRID 1903941Notes

Reaction equation

HRID 1903941 reaction equation
[OH:1][CH2:2][CH2:3]CCCC1CCCC1=O.OCCCCCC1CCCC1=O.[C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])(=[O:27])[CH3:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(=O)C)(=O)C>>[C:2]([O:39][C:35]1[CH2:36][CH2:37][CH2:38][C:34]=1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][C:25](=[O:27])[CH3:26])(=[O:1])[CH3:3]

Participants

5

Reactant 4

HCID 7918Acetic Anhydride2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 204655182-(5-Hydroxypentyl)cyclopentan-1-oneHCID 867329372-(5-Hydroxypentyl)cyclopentanone 2-(5-acetoxypentyl)-cyclopentanone

Product 1

HCID 20465612HCID 20465612, compound

Procedure

A solution of 400 g. (2.04 moles, of a mixture of 2-(5-hydroxypentyl)cyclopentanone and 2-(5-acetoxypentyl)cyclopentanone (Example 55) and 4.0 g. of p-toluenesulfonic acid monohydrate in 1 l. of acetic anhydride is refluxed at a rate to maintain a steady distillation of acetic acid from the reaction through a helix-packed fractionation column. The reaction is continued with the addition of acetic anhydride to maintain a constant volume until complete conversion of starting materials to product is evident. The mixture is cooled and partitioned between 2 l. of hexane and 3 l. of cold water containing solid sodium bicarbonate to maintain a neutral pH. The organic phase is washed with saturated brine, dried (MgSO4), and evaporated to yield 452 g. of an oil.

Workup

  1. temperatureto maintain
  2. distillationa steady distillation of acetic acid
  3. customfrom the reaction through a helix-packed fractionation column
  4. temperatureto maintain a constant volume until complete conversion of starting materials to product
  5. temperatureThe mixture is cooled
  6. custompartitioned between 2 l
  7. temperatureof cold water containing solid sodium bicarbonate to maintain a neutral pH
  8. washThe organic phase is washed with saturated brine
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customto yield 452 g

Sources & evidence

ORD record
ord-bb1f5bd09fd54d50bbf826de569724a7
Source dataset
uspto-grants-1984_03
Patent number
US04439365

Reaction notes

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