Quinone → 1,2,3,4,8a,9,10,10a-Octahydro-2,3-dimethylene-1,4-epoxyanthracene-5,8-dione

HRID 1154768Notes

Reaction equation

[CH2:1]=[C:2]1[C:7](=[CH2:8])[CH:6]2[O:9][CH:3]1[C:4](=[CH2:11])[C:5]2=[CH2:10].[C:12]1(=[O:19])[CH:17]=[CH:16][C:15](=[O:18])[CH:14]=[CH:13]1>C(Cl)(Cl)Cl>[CH2:11]=[C:4]1[C:5](=[CH2:10])[CH:6]2[O:9][CH:3]1[C:2]1[CH2:1][CH:17]3[CH:16]([CH2:8][C:7]=12)[C:15](=[O:18])[CH:14]=[CH:13][C:12]3=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2 g (13.7 mmol) of 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane, 1.47 g (13.7 mmol) of freshly sublimed p-benzoquinone and 20 ml of chloroform was heated at 80° C. for 5 hours under nitrogen. After cooling, the mixture was concentrated to dryness and recrystallised from acetone/methanol (4:1). There were obtained 3.28 g (95%) of 1,2,3,4,8a,9,10,10a-octahydro-2,3-dimethylene-1,4-epoxyanthracene-5,8-dione of melting point 147° C. (decomposition) in the form of yellow crystals.

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated to dryness
customrecrystallised from acetone/methanol (4:1)

Sources & evidence

ORD record: ord-348e696a5cc44ef0938de0d38b1344c8
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04298535

Reaction notes

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