(-)-alpha-Pinene → HCID 68865089, compound

HRID 1454763Notes

Reaction equation

HRID 1454763 reaction equation
[C:1](Cl)(=[O:6])[CH:2]=[CH:3][CH2:4][CH3:5].[CH3:8][C:9]1[C@H:14]2[C:15]([CH3:17])([CH3:16])[C@H:12]([CH2:13]2)[CH2:11][CH:10]=1>C(Cl)CCl.[Cl-].[Zn+2].[Cl-]>[CH2:4]([CH:3]1[C:12]2([C:15]([CH3:17])=[CH2:16])[CH2:13][CH:14]([C:9]([CH3:8])=[CH:10][CH2:11]2)[C:1](=[O:6])[CH2:2]1)[CH3:5]

Participants

5

Reactant 2

HCID 440968(-)-alpha-PineneHCID 2760310HCID 2760310, compound

Product 1

HCID 68865089HCID 68865089, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
30 °C

Procedure

At 30° C., a mixture of 7.35 g of 2-pentenoyl chloride (62 mmol) and 1.7 g of zinc chloride (12 mmol, 0.2 eq.) in 85 ml ethylene chloride was treated dropwise within 20 min. with a solution of 19.4 g of (−)-alpha-pinene (142 mmol, 2 eq.) in 20 ml ethylene dichloride. The reaction mixture was then stirred at 30° C. for 30 min., then at 50° C. for 2 h, and finally at 80° C. for 1 h. After cooling, the reaction mixture was washed with aq. sat. NaCl soln. and aq. sat. NaHCO3 soln. The aq. phases were extracted with Et2O, dried (Na2SO4), and concentrated. FC (SiO2, hexane/Et2O 20:1) of the crude (26 g) gave 1.74 g (13%) of compound 2. The boiling point of the end product is 95° C. at 0.06 torr (0.08 mbar).

Workup

  1. waitat 50° C. for 2 h
  2. waitfinally at 80° C. for 1 h
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with aq. sat. NaCl soln
  5. extractionThe aq. phases were extracted with Et2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0cc09c91503d417bb37f81ea6b3e7f59
Source dataset
uspto-grants-2009_01
Patent number
US07482313B2

Reaction notes

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