HCID 15029625, compound → HCID 15029626, compound

HRID 1757386Notes

Reaction equation

HRID 1757386 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 of4.05 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 withacetonitrile and then water before vacuum drying at room temperature to give 0.057 g of yellow solid. mp 172.0°-173.2°; 1H NMR(CDCl): 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-5bfc59145b124e808edadf84ea3eea5f
Source dataset
uspto-grants-1995_08
Patent number
US05446039

Reaction notes

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