4-Hydroxybenzoic Acid → HCID 59434464, compound

HRID 1014900Notes

Reaction equation

HRID 1014900 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.O[C:17]1[CH:29]=[CH:28][C:27]2[C:26]3[C:21](=[CH:22][C:23]([OH:30])=[CH:24][CH:25]=3)[C:20]([CH3:32])([CH3:31])[C:19]=2[CH:18]=1.B(O)(O)O>C1(C)C(C)=CC=CC=1>[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][C:17]2[CH:29]=[CH:28][C:27]3[C:26]4[C:21](=[CH:22][C:23]([O:30][C:11](=[O:12])[C:10]5[CH:14]=[CH:15][C:7]([OH:6])=[CH:8][CH:9]=5)=[CH:24][CH:25]=4)[C:20]([CH3:32])([CH3:31])[C:19]=3[CH:18]=2)=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 272821199,9-Dimethyl-9H-fluorene-2,7-diol

Product 1

HCID 59434464HCID 59434464, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In a nitrogen atmosphere, concentrated sulfuric acid (0.2 mL) was added to a mixture of 4-hydroxybenzoic acid (12.2 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-hydroxybenzoyloxy)-9,9-dimethylfluorene (compound [H2]) (17.6 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-7d2eaa0a423c4029987b57d9cfd1cb47
Source dataset
uspto-grants-2011_07
Patent number
US07985455B2

Reaction notes

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