2,5-Di-tert-butylhydroquinone → rac-(3aR,4S,7R,7aS)-3a,4,7,7a-tetrahydro-4,7-ethanoindene-1,3-dione

HRID 1415573

Reaction equation

HRID 1415573 reaction equation
[C:1]1(=[O:7])[CH:5]=[CH:4][C:3](=[O:6])[CH2:2]1.[CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH:9]=1.C(C1C=C(O)C(C(C)(C)C)=CC=1O)(C)(C)C>C1C=CC=CC=1>[CH:10]12[CH2:11][CH2:12][CH:13]([CH:8]=[CH:9]1)[CH:4]1[CH:5]2[C:1](=[O:7])[CH2:2][C:3]1=[O:6]

Participants

5

Reactant 3

HCID 23742,5-Di-tert-butylhydroquinoneHCID 116051,3-CyclohexadieneHCID 702582-Cyclopentene-1,4-dione

Product 1

HCID 53663301rac-(3aR,4S,7R,7aS)-3a,4,7,7a-tetrahydro-4,7-ethanoindene-1,3-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-cyclopentene-1,3-dione (7.0g; 0.073 mole) in dry benzene (20ml.) was added to 1,3-cyclohexadiene (12g; 0.15 mole). After addition of a few crystals of 2,5-ditert-butyl hydroquinone the stoppered mixture was stood at room temperature for 4 days. Removal of the solid and recrystallisation from methanol gave the adduct m.p. 264°.

Workup

  1. customRemoval of the solid and recrystallisation from methanol

Sources & evidence

ORD record
ord-6c34422ce8e7441bb88be0522ae7724d
Source dataset
uspto-grants-1977_01
Patent number
US04005219

Linked notes

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