4-Hydroxybenzoic Acid → 2,7-Bis(4-hydroxybenzoyloxy)-9-methylfluorene

HRID 1014899Notes

Reaction equation

HRID 1014899 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.[OH:16][C:17]1[CH:29]=[CH:28][C:27]2[C:26]3[C:21](=[CH:22][C:23](O)=[CH:24][CH:25]=3)[CH:20]([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:23]2[CH:24]=[CH:25][C:26]3[C:27]4[C:19](=[CH:18][C:17]([O:16][C:11](=[O:12])[C:10]5[CH:14]=[CH:15][C:7]([OH:6])=[CH:8][CH:9]=5)=[CH:29][CH:28]=4)[CH:20]([CH3:31])[C:21]=3[CH:22]=2)=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 219606279-methyl-9H-fluorene-2,7-diol

Product 1

HCID 594344632,7-Bis(4-hydroxybenzoyloxy)-9-methylfluoreneYield 70%

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 (13.0 g), 2,7-dihydroxy-9-methylfluorene (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 solid matter thus deposited was collected by filtration under reduced pressure, and rinsed with toluene. The solid matter was recrystallized from a mixed solvent of ethanol (75 mL) and acetone (75 mL) to provide 2,7-bis(4-hydroxybenzoyloxy)-9-methylfluorene (compound [H1]) (14.9 g) in the form of pale rose crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customwhile removing water
  4. filtrationA solid matter thus deposited was collected by filtration under reduced pressure
  5. washrinsed with toluene
  6. customThe solid matter was recrystallized from a mixed solvent of ethanol (75 mL) and acetone (75 mL)

Sources & evidence

ORD record
ord-13e26a18a2c44b1a91829a7d0d1611b0
Source dataset
uspto-grants-2011_07
Patent number
US07985455B2

Reaction notes

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