HCID 15029625, compound → HCID 15029626, compound

HRID 1736635Notes

Reaction equation

HRID 1736635 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])=[CH:5][C:6]([O:14][CH:15]([CH3:17])[CH3:16])=[C:7]2[OH:13]>C(OCC)C.O.C(O)(C)C>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:18])[CH:5]=[C:6]([O:14][CH:15]([CH3:16])[CH3:17])[C:7]2=[O:13]

Participants

5

Reactant 1

HCID 15029625HCID 15029625, compound

Product 1

HCID 15029626HCID 15029626, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 0.55 g (2.1 mM) of 5,7-difluoro-1,4-dihydroxy-2-isopropoxy-naphthalene in 20 mL of diethyl ether was added over 0.05 hours to a stirred, room temperature solution of 4.05 g (25 mM) of ferric chloride in 46 mL of water and 12 mL of isopropanol. The mixture was stirred for 0.75 hours and then extracted with ethyl acetate. The organic extracts were dried with sodium sulfate, filtered and concentrated to give 0.44 g of tan solid which was recrystalized from 3 mL of warm acetic acid and a few drops of water. After cooling to room temperature, the solid was filtered off, washed with acetonitrile and then water before vacuum drying at room temperature to give 0.057 g of yellow solid. mp 172.0°-173.2°; 1H NMR (CDCl3): δ=7.68 (dd, 1H), 7.15 (m, 1H), 6.09 (s, 1H), 4.55 (m, 1H), 1.45(d, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-028b58d6bf99404bb202cb6da0042815
Source dataset
uspto-grants-1996_07
Patent number
US05541319

Reaction notes

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