1,4,4a,9a-Tetrahydroanthracene-9,10-dione → HCID 18688925, compound

HRID 1902763Notes

Reaction equation

HRID 1902763 reaction equation
[CH2:1]1[CH:14]2[CH:5]([C:6](=[O:16])[C:7]3[C:12]([C:13]2=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH:3]=[CH:2]1.[H][H]>[Pd].C(O)(=O)C>[CH2:4]1[C:5]2[C:14](=[C:13]([OH:15])[C:12]3[C:7]([C:6]=2[OH:16])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 920211,4,4a,9a-Tetrahydroanthracene-9,10-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 18688925HCID 18688925, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

300 ml of acetic acid, 64 g of 1,4,4a,9a-tetrahydro-anthraquinone and 0.6 g of a catalyst containing 5% of palladium deposited on charcoal are introduced into an autoclave. The charge is heated to 100° C. and hydrogen is introduced under a pressure of 30 bars. The reaction is continued for 4 hours while maintaining the pressure at between 20 and 30 bars. After cooling, the precipitate obtained is separated by filtration, washed with water and dried. 56 Grams of 1,2,3,4-tetrahydro-9,10-anthracene-diol (melting point 210°-212° C.) are obtained. The yield is 86.7% without taking into account the fraction of product remaining in solution in the acetic acid.

Workup

  1. additionare introduced into an autoclave
  2. temperaturewhile maintaining the pressure at between 20 and 30 bars
  3. temperatureAfter cooling
  4. customthe precipitate obtained
  5. customis separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b2b73f108b0c4ea4a8fa52b6bcf70f1b
Source dataset
uspto-grants-1982_12
Patent number
US04365100

Reaction notes

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