Hydrochloric Acid → 7-Hydroxy-9-methyl-9H-fluoren-2-YL 4-(octyloxy)benzoate

HRID 130270Notes

Reaction equation

HRID 130270 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1C(Cl)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O:19]1CCC[CH2:20]1.[OH:24][C:25]1[CH:37]=[CH:36][C:35]2[C:34]3[C:29](=[CH:30][C:31]([OH:38])=[CH:32][CH:33]=3)[CH:28]([CH3:39])[C:27]=2[CH:26]=1.Cl>N1C=CC=CC=1>[CH2:1]([O:9][C:10]1[CH:11]=[CH:15][C:16]([C:20]([O:24][C:25]2[CH:37]=[CH:36][C:35]3[C:34]4[C:29](=[CH:30][C:31]([OH:38])=[CH:32][CH:33]=4)[CH:28]([CH3:39])[C:27]=3[CH:26]=2)=[O:19])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 203111572-(Octyloxy)benzoyl chlorideHCID 219606279-methyl-9H-fluorene-2,7-diol

Product 1

HCID 585869377-Hydroxy-9-methyl-9H-fluoren-2-YL 4-(octyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Octyloxybenzoic acid chloride 12.5 g was added dividing into several times to a tetrahydrofuran (100 ml) solution of 2,7-dihydroxy-9-methylfluorene 10 g and pyridine 8 g, and the solution was refluxed for 5 hours. 5% hydrochloric acid 50 ml was added to the reaction mixture, and the solution was extracted with methylene chloride. The extract was washed with 5% hydrochloric acid until pH became acidic, and then it was washed with a saturated sodium hydrogencarbonate aqueous solution and dried on anhydrous magnesium sulfate. A residue obtained by distilling the solvent off was refined by silica gel column chromatography (eluent solvent: methylene chloride) to obtain 10 g of 2-(4-octyloxybenzoyloxy)-7-hydroxy-9-methylfluorene (J1). Melting point: 140 to 143° C.

Workup

  1. temperaturethe solution was refluxed for 5 hours
  2. extractionthe solution was extracted with methylene chloride
  3. washThe extract was washed with 5% hydrochloric acid until pH
  4. washit was washed with a saturated sodium hydrogencarbonate aqueous solution
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customA residue obtained
  7. distillationby distilling the solvent

Sources & evidence

ORD record
ord-0b7db84dabb84b8ea727ab62346d2823
Source dataset
uspto-grants-2008_06
Patent number
US07381350B2

Reaction notes

Loading…