Sulfuric Acid → HCID 59434470, compound

HRID 1014901Notes

Reaction equation

HRID 1014901 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].O[C:18]1[CH:30]=[CH:29][C:28]2[C:27]3[C:22](=[CH:23][C:24]([OH:31])=[CH:25][CH:26]=3)[C:21]([CH3:33])([CH3:32])[C:20]=2[CH:19]=1.B(O)(O)O>C1(C)C(C)=CC=CC=1>[OH:16][C:14]1[CH:13]=[CH:12][C:8]([C:9]([O:31][C:24]2[CH:25]=[CH:26][C:27]3[C:28]4[C:20](=[CH:19][C:18]([O:10][C:9](=[O:11])[C:8]5[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:7]=5[F:6])=[CH:30][CH:29]=4)[C:21]([CH3:32])([CH3:33])[C:22]=3[CH:23]=2)=[O:10])=[C:7]([F:6])[CH:15]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 27833982-Fluoro-4-hydroxybenzoic AcidHCID 272821199,9-Dimethyl-9H-fluorene-2,7-diol

Product 1

HCID 59434470HCID 59434470, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In a nitrogen atmosphere, concentrated sulfuric acid (0.2 mL) was added to a mixture of 2-fluoro-4-hydroxybenzoic acid (13.8 g), 2,7-dihydroxy-9,9-dimethylfluorene (10.0 g), boric acid (0.3 g) and xylene (120 mL), and the mixture was heated under reflux for 6 hours while removing water. A deposited matter was filtered and rinsed with toluene. It was recrystallized from a mixed solvent of ethanol (75 mL) and acetone (75 mL) to provide 2,7-bis(4-hydroxy-2-fluorobenzoyloxy)-9,9-dimethylfluorene (compound [H3]) (7.77 g) in the form of pale rose solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customwhile removing water
  4. filtrationA deposited matter was filtered
  5. washrinsed with toluene
  6. customIt was recrystallized from a mixed solvent of ethanol (75 mL) and acetone (75 mL)

Sources & evidence

ORD record
ord-b3e829b11c7e4587953876d79ca6080c
Source dataset
uspto-grants-2011_07
Patent number
US07985455B2

Reaction notes

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