Hydrochloric Acid → 1,3,8-Trihydroxy-6-methyl-9(10H)-anthracenone

HRID 470658Notes

Reaction equation

HRID 470658 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]2[C:9]([C:11]3[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=3[C:19](=O)[C:4]=2[CH:3]=1)=[O:10].Cl>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]2[C:9]([C:11]3[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=3[CH2:19][C:4]=2[CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 3220Emodin

Product 1

HCID 1226351,3,8-Trihydroxy-6-methyl-9(10H)-anthracenoneYield 95.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 20 grams of emodin, 1000 mL of acetic acid, 82.8 grams of stannous chloride was heated to reflux. Hydrochloric acid (60 mL) was added slowly in minutes and continued reflux for 1 hour. Remaining 167 mL of HCl was added slowly at reflux and continued for an additional 1 hour. Orange color mixture was cooled to room temperature and left over night. Product was isolated by filtration and washed with water. Finally the product (emodin anthrone) was dried in vacuo at 60° C. to a constant weight to afford 18.1 grams (Yield: 95%) of an orange powder.

Workup

  1. temperaturewas heated to reflux
  2. temperaturecontinued reflux for 1 hour
  3. additionwas added slowly
  4. temperatureat reflux
  5. waitleft over night
  6. customProduct was isolated by filtration
  7. washwashed with water
  8. dry with materialFinally the product (emodin anthrone) was dried in vacuo at 60° C. to a constant weight

Sources & evidence

ORD record
ord-6f789f8da53a432bad8ff41fd920e6e6
Source dataset
uspto-grants-2014_01
Patent number
US08629302B2

Reaction notes

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