Acetic Anhydride → HCID 69197522, compound

HRID 132781Notes

Reaction equation

HRID 132781 reaction equation
[CH2:1]([C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH:4]1[OH:8])[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(Cl)Cl.S(=O)(=O)(O)O>[CH2:1]([C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH:4]1[O:8][C:14](=[O:16])[CH3:15])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 69198385HCID 69198385, compound

Product 1

HCID 69197522HCID 69197522, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

5.58 grams of ethyl 1-ethyl-2-hydroxy-cyclopentane carboxylate obtained in Example 15 was diluted with 50 ml of methylene chloride. To the solution were added several drops of concentrated sulfuric acid, then dropwise added 4.32 ml of acetic anhydride. The mixture was allowed to react under reflux condition for 2 hours. The reaction mixture was washed with 50 ml of ethyl acetate and 50 ml of water, and organic layer was separated. Then the organic layer was washed with 10% aqueous solution of sodium carbonate twice, then with saline solution to neutrality, and dried over anhydrous magnesium sulfate. Removing solvent gave 5.91 g of colorless liquid. Yield after chromatography purification: 83.20%. MS: m/e 228(M+′), 183(M+—OCH2CH3), 169 (M+—CH3CO2), 158, 155, 140, 129, 113, 101.

Workup

  1. customto react
  2. temperatureunder reflux condition for 2 hours
  3. washThe reaction mixture was washed with 50 ml of ethyl acetate and 50 ml of water, and organic layer
  4. customwas separated
  5. washThen the organic layer was washed with 10% aqueous solution of sodium carbonate twice
  6. dry with materialwith saline solution to neutrality, and dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-5f731cb092e0483eac3fcb6a3a25a6e8
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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