1-Butanol → alpha-Pinene oxide

HRID 1454216Notes

Reaction equation

HRID 1454216 reaction equation
[CH3:1]OC(=O)CC(C)=O.[CH2:9]([OH:13])[CH2:10][CH2:11][CH3:12].C(OCCCC)(=O)CC(C)=O.[C:25]1([CH3:31])[CH:30]=CC=[CH:27][CH:26]=1>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]>[CH3:30][C:25]1([CH3:31])[CH:11]2[C:10]3([CH3:1])[O:13][CH:9]3[CH2:27][CH:26]1[CH2:12]2

Participants

6

Reactant 4

HCID 2631-ButanolHCID 1140TolueneHCID 7757Methyl acetoacetateHCID 11576Butyl acetoacetate

Product 1

HCID 91508alpha-Pinene oxide

Reagents, catalysts & solvents 1

HCID 7611Bis(eta-cyclopentadienyl) ironCatalyst

Conditions

Temperature
30 °C

Procedure

2.1 mL of methylacetoacetate (20 mmol) and 1.8 mL of n-butanol (20 mmol) were added into 20 mL of toluene and stirred at 30° C. and 400 rpm for 15 minutes. 155 mg of the catalyst (FerlipaseCB(7) polymer beads) prepared in (2) was added into the mixture to initiate reaction. A clear liquid sample was periodically sampled and analyzed using gas chromatography to identify n-butyl acetoacetate, which was the reaction product.

Workup

  1. additionwas added into the mixture
  2. customreaction
  3. aliquotA clear liquid sample was periodically sampled

Sources & evidence

ORD record
ord-11738d36c00a47198277e7d9528f542a
Source dataset
uspto-grants-2009_01
Patent number
US07479254B2

Reaction notes

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