Ethanol → HCID 21459175, compound

HRID 2260291Notes

Reaction equation

HRID 2260291 reaction equation
B(Br)(Br)Br.[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:29])[CH2:13][C:14]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([O:25]C)=[C:18]([O:27]C)[CH:17]=1)=[O:15].C(O)C>C(Cl)Cl>[OH:27][C:18]1[CH:17]=[C:16]([C:14](=[O:15])[CH2:13][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[OH:5])=[O:29])[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]=1[OH:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 21459120HCID 21459120, compound

Product 1

HCID 21459175HCID 21459175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.82 g of boron tribromide in 20 ml of methylene chloride is added dropwise within about 20 minutes to a solution of 500 mg of 1-(o-hydroxyphenyl)-3-(3,4-dimethoxy-5-nitrophenyl)-1,3-propanedione in 50 ml of methylene chloride while stirring and under an argon atmosphere at -20°, whereupon the mixture is stirred at room temperature overnight. After cooling to -20° the mixture is treated dropwise with 25 ml of ethanol and evaporated at 40° in a water-jet vacuum. After recrystallization from ethanol, there is obtained 1-(3,4-dihydroxy-5-nitrophenyl)-3-(o-hydroxyphenyl)-1,3-propanedione in the form of yellow crystals of m.p. 251°-252°.

Workup

  1. stirringis stirred at room temperature overnight
  2. temperatureAfter cooling to -20° the mixture
  3. customevaporated at 40° in a water-jet vacuum
  4. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-c91f190dac2148c6ac9582d557aaa522
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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