Salicylic Acid → 1,3-Dihydroxy-xanthone

HRID 83092

Reaction equation

HRID 83092 reaction equation
[C:1](O)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O.[C:11]1([CH:19]=[C:17]([OH:18])[CH:16]=[C:14]([OH:15])[CH:13]=1)[OH:12]>>[OH:12][C:11]1[C:19]2[C:1](=[O:9])[C:2]3[C:8](=[CH:7][CH:6]=[CH:5][CH:3]=3)[O:18][C:17]=2[CH:16]=[C:14]([OH:15])[CH:13]=1

Participants

3

Reactant 2

HCID 338Salicylic AcidHCID 359Phloroglucinol

Product 1

HCID 54881931,3-Dihydroxy-xanthoneYield 93.4%

Conditions

Temperature
80 °C

Procedure

Salicylic acid (1.25 g, 9.1 mmol), phloroglucinol (1.26 g, 10 mmol), ZnCl□(3.1 g, 22.8 mmol) and POCl□ (8 mL) were charged to a dry round-bottom flask, and the reaction mixture was stirred at 80° C. for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and was very slowly added to ice water. When the reaction liquid was poured in ice water, ice was added portionwise to prevent overheating. The resulting precipitate was allowed to stand at 4° C. overnight, combined, washed with water and ether, and then dried under reduced pressure to give a reddish brown solid compound (1.94 g, 93%).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customWhen the reaction liquid
  3. additionice was added portionwise
  4. waitto stand at 4° C. overnight
  5. washwashed with water and ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d4c5ccb4eec247519b3c0bf411d20f5b
Source dataset
uspto-grants-2014_09
Patent number
US08846749B2

Linked notes

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