Ethyl Acetate → 1,4-Ethanonaphthalen-2(1H)-one, 3,4-dihydro-

HRID 1879347

Reaction equation

HRID 1879347 reaction equation
[CH:1]12[CH2:13][CH2:12][CH:8]([CH:9]([OH:11])[CH2:10]1)[C:7]1[C:2]2=[CH:3][CH:4]=[CH:5][CH:6]=1.CCOC(C)=O>C(Cl)Cl>[CH:1]12[CH2:13][CH2:12][CH:8]([C:9](=[O:11])[CH2:10]1)[C:7]1[C:2]2=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 5826161,4-Ethanonaphthalen-2-ol, 1,2,3,4-tetrahydro-, exo-

Product 1

HCID 5825961,4-Ethanonaphthalen-2(1H)-one, 3,4-dihydro-Yield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.6 g of tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol in 30 mL of DCM were added 110 mL of a 15% DMP solution in DCM. After stirring overnight 300 mL of EtOAc/Hept (1:1) were added, the obtained suspension was filtered over a pad of celite and the filtrated was concentrated in vacuo. The residue was treated again with EtOAc/Hept (1:1) and filtered over celite. This procedure was repeated twice to obtain 4.9 g of the desired compound as yellow oil.

Workup

  1. additionwere added
  2. filtrationthe obtained suspension was filtered over a pad of celite
  3. concentrationthe filtrated was concentrated in vacuo
  4. additionThe residue was treated again with EtOAc/Hept (1:1)
  5. filtrationfiltered over celite

Sources & evidence

ORD record
ord-327b7c94f4314aa39944ec100ec8d2af
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Linked notes

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