Water → HCID 23511677, compound

HRID 353700Notes

Reaction equation

COC1C=CC2C3C=C4C=CC(OC)=CC4=C(O)C=3CC=2C=1.[CH3:23][O:24][C:25]1[CH:45]=[CH:44][C:28]2[C:29]3[C:38]([CH2:39][CH2:40][C:27]=2[CH:26]=1)=[C:37]([OH:41])[C:36]1[C:31](=[CH:32][CH:33]=[C:34]([O:42][CH3:43])[CH:35]=1)[CH:30]=3.[Cl:46]C1C(=O)C(Cl)=C(Cl)C(Cl)(Cl)C=1Cl.O>CN(C=O)C>[CH3:23][O:24][C:25]1[CH:45]=[CH:44][C:28]2[C:29]3[C:38]([CH2:39][CH2:40][C:27]=2[CH:26]=1)=[C:37]([OH:41])[C:36]1[C:31](=[CH:32][CH:33]=[C:34]([O:42][CH3:43])[CH:35]=1)[CH:30]=3.[Cl:46][C:30]1[C:31]2[C:36]([C:37]([OH:41])=[C:38]3[C:29]=1[C:28]1[CH:44]=[CH:45][C:25]([O:24][CH3:23])=[CH:26][C:27]=1[CH2:40][CH2:39]3)=[CH:35][C:34]([O:42][CH3:43])=[CH:33][CH:32]=2

Participants

Conditions

Temperature: 40 °C

Procedure

The compound 3,9-dimethoxy-7-hydroxy-5,6-dihydro-benz[a]anthracene (compounds 23) was prepared analogously to compound 16 in example 5. To a solution of 600 mg of 23 in 10 ml of DMF was added in portions 600 mg of 2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one. The mixture was then stirred at 40° C. for 4 hr. Then the reaction was poured into water and the product extracted with ethyl acetate. The crude material was passed through a silicagel column (hept./eth.ac.) and finally triturated with heptane-diisopropyl ether to provide 280 mg of 24 as orange crystals; Mp 140-141° C., Rf 0.28 (hept./eth.ac. 7/3) starting material Rf 0.30.

Workup

extractionthe product extracted with ethyl acetate
customfinally triturated with heptane-diisopropyl ether

Sources & evidence

ORD record: ord-99c848094b1b4232929d5bca971fde5d
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756375B2

Reaction notes

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