Acetic Anhydride → HCID 20465612, compound

HRID 328509Notes

Reaction equation

HRID 328509 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 29) 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-c26f6862d7d04ee0826bbf9095f33acd
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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