Ethanol → 6,11-Dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione

HRID 649278Notes

Reaction equation

[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2C(O)=C[CH:3]=1.[C:13](Cl)(=[O:23])[C:14]1[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:16](Cl)=[O:17].[CH3:25][CH2:26][OH:27]>>[OH:27][C:26]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:2]([OH:1])=[C:3]2[C:25]=1[C:13](=[O:23])[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]2=[O:17]

Participants

Reactant 3

HCID 702Ethanol

HCID 6955Phthaloyl chloride

HCID 836221,4-Naphthalenediol, 5,6,7,8-tetrahydro-

Product 1

HCID 4192906,11-Dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dioneYield 88%

Procedure

The method was similar to Example 1 but using 16.4 g (0.1 mols) of 1,4-dihydroxy-5,6,7,8-tetrahydronaphthalene and 20.2 g (0.1 mol) of phthalic acid dichloride. The product was 33.7 g (88% yield) of 6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphtacenequinone (9), m.p.=194°-196° C. (EtOH).

Sources & evidence

ORD record: ord-7096ba54468f407297ec2989809e6acc
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04739062

Reaction notes

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