Phloroglucinol → 1,3-dihydroxy-5-methoxy-9H-xanthen-9-one

HRID 83089

Reaction equation

HRID 83089 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[C:14]1([CH:22]=C(O)[CH:19]=[C:17]([OH:18])[CH:16]=1)[OH:15]>>[OH:15][C:14]1[C:22]2[C:5](=[O:7])[C:4]3[C:3](=[C:11]([O:12][CH3:13])[CH:10]=[CH:9][CH:8]=3)[O:2][C:1]=2[CH:19]=[C:17]([OH:18])[CH:16]=1

Participants

3

Reactant 2

HCID 359PhloroglucinolHCID 152042,3-Dimethoxybenzoic acid

Product 1

HCID 120264891,3-dihydroxy-5-methoxy-9H-xanthen-9-oneYield 94.8%

Conditions

Temperature
80 °C

Procedure

2,3-dimethoxybenzoic acid (0.91 g, 5 mmol), phloroglucinol (0.95 g, 7.5 mmol), ZnCl□ (4.69 g, 30 mmol) and POCl□ (20 mL) were charged to a dry round-bottom flask, followed by stirring 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 500 mL of 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 the title compound (1.22 g, 94.8%) as a reddish brown solid.

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-88281e7637434075ba1a3856a89d84a5
Source dataset
uspto-grants-2014_09
Patent number
US08846749B2

Linked notes

Loading…