Ethanol → HCID 68771264, compound

HRID 1170947

Reaction equation

HRID 1170947 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3.C(O)C.[OH-].[K+].[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)([F:26])([F:25])[F:24]>O>[F:24][C:23]([F:26])([F:25])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium Hydroxide2×HCID 57493223,6-dihydroxy-9H-xanthen-9-oneHCID 138454716-Bromo-1,1,1-trifluorohexane

Product 1

HCID 68771264HCID 68771264, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3,6-dihydroxy-xanthone (0.58 g, 1 equivalent) is added 10 ml of ethanol, then 117 mg of KOH 0.8 equivalents), followed by 0.58 g of CF3(CH2)5Br (1 equivalent); after two hours of boiling this mixture, the pH had dropped to the acidic range, and another 100 mg of KOH was added and heating continued overnight. The cooled mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml), the combined extracts washed with 5 ml of water and brought to dryness. Separation of the 3-component mixture was achieved by chromatography (100 g of silica gel, column diameter 5 cm) with solvents of increasing polarity: Solvents used: ethyl acetate (A), hexane (isomeric mixture) (B), ethanol (C)

Workup

  1. additionthe pH had dropped to the acidic range
  2. temperatureheating continued overnight
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washthe combined extracts washed with 5 ml of water
  5. customSeparation of the 3-component mixture
  6. temperatureof increasing polarity

Sources & evidence

ORD record
ord-632095f8161a4f4bb137138c227a7b63
Source dataset
uspto-grants-2010_11
Patent number
US07829578B1

Linked notes

Loading…