Water → Fluoreneone

HRID 2211362Notes

Reaction equation

HRID 2211362 reaction equation
[CH:1]1[C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1([OH:21])C=CC=CC=1.O.C1(CC2C=CC=CC=2)C=CC=CC=1.SCCCS(O)(=O)=O>>[C:1]1(=[O:21])[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1

Participants

6

Reactant 5

HCID 962WaterHCID 996PhenolHCID 7580DiphenylmethaneHCID 10241FluorenoneHCID 872061-Propanesulfonic acid, 3-mercapto-

Product 1

HCID 22281833Fluoreneone

Conditions

Temperature
53 °C

Procedure

9-Fluorenone (3.65 g, 0.020 mol, 1.0 equiv.), molten phenol (39.6 g, 0.420 mol, 20.8 equiv.), deionized water (0.362 g, 20.1 mmol, 0.994 equiv.) and diphenylmethane (32.83 g) is added to the reactor (reactor design 2). The reaction mixture is heated to 53° C. with stirring under a pad of nitrogen. 3-Mercaptopropanesulfonic acid (0.158 g, 1.00 mmol, 0.0500 equiv.) is added slowly over approximately 1 minute to the reaction mixture at 53° C. The reaction is monitored throughout the reaction period by collecting samples and analyzing by HPLC. The 9-fluorenone is found to be 25% consumed within 2 hours, 45% consumed within 4.5 hours, and 57% consumed within 6 hours. HPLC analysis (analytical method 3) gives the following relative area % analysis for the reaction products (fluorenone area not included) at 57% conversion:

Workup

  1. customThe reaction is monitored throughout the reaction period
  2. customby collecting samples
  3. customconsumed within 2 hours
  4. custom45% consumed within 4.5 hours
  5. custom57% consumed within 6 hours

Sources & evidence

ORD record
ord-678c2ac370c1411eb3d50652ce2e056d
Source dataset
uspto-grants-1995_10
Patent number
US05463140

Reaction notes

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