Acetic Anhydride → HCID 68725178, compound

HRID 1471379Notes

Reaction equation

HRID 1471379 reaction equation
[CH3:1][C:2]1[CH2:9][CH2:8][CH2:7][C:4]2([CH2:6][CH2:5]2)[CH:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].C([O-])(O)=O.[Na+]>[Cl-].[Zn+2].[Cl-]>[CH3:1][C:2]1[CH2:9][CH2:8][CH2:7][C:4]2([CH2:6][CH2:5]2)[CH:3]=1.[CH3:1][C:2]1[CH:3]([C:10](=[O:12])[CH3:11])[C:4]2([CH2:7][CH2:8][CH:9]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 86647583HCID 86647583, compound

Product 2

HCID 68725178HCID 68725178, compoundYield 25%HCID 86647583HCID 86647583, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
50 °C

Procedure

A mixture of 5-methylspiro[2.5]oct-4-ene (1.41 g, 11.5 mmol), acetic anhydride (2.83 ml, 29.9 mmol), and zinc chloride (203 mg, 1.5 mmol) was heated at 50° C. for 14.5 h, cooled to 20° C., poured into a mixture of a saturated aqueous solution of NaHCO3 and ice, and extracted with pentane. The aqueous phase was extracted twice with pentane and the combined organic phases were washed with a saturated aqueous solution of NH4Cl, with a saturated aqueous solution of NaCl, dried (Na2SO4), and concentrated. FC (300 g SiO2, pentane/Et2O10:0.5) of the crude product (1.91 g) gave unreacted 5-methylspiro[2.5]oct-4-ene (765 mg) and 1-(5-methylspiro[2.5]oct-5-en-4-yl)ethanone (479 mg, 25%).

Workup

  1. temperaturecooled to 20° C.
  2. extractionextracted with pentane
  3. extractionThe aqueous phase was extracted twice with pentane
  4. washthe combined organic phases were washed with a saturated aqueous solution of NH4Cl, with a saturated aqueous solution of NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-308165bb80454214a1e4cc2fe9922a64
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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