Water → Fluoreneone

HRID 367002Notes

Reaction equation

HRID 367002 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, 0.0200 mol, 1.00 equiv.), molten phenol (39.6 g, 0.420 mol, 20.8 equiv.), deionized water (1.09 g, 60.7 mmol, 3.00 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 11% consumed within 2 hours, 20% consumed within 4.5 hours, and 23% consumed within 6 hours. HPLC analysis (analytical method 3) gives the following relative area % analysis for the reaction products (fluorenone area not included) at 23% conversion:

Workup

  1. customThe reaction is monitored throughout the reaction period
  2. customby collecting samples
  3. customconsumed within 2 hours
  4. custom20% consumed within 4.5 hours
  5. custom23% consumed within 6 hours

Sources & evidence

ORD record
ord-ffcf17a5ed184861a2ba0ef83b069874
Source dataset
uspto-grants-2000_10
Patent number
US06133190

Reaction notes

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