Water → Fluoreneone

HRID 1585773Notes

Reaction equation

HRID 1585773 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 (0.055 g, 3.06 mmol, 0.151 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 (0.170 g, 1.10 mmol, 0.0537 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 49% consumed within 2 hours and 77% consumed within 4.5 hours. HPLC analysis (analytical method 3) gives the following relative area % analysis for the reaction products (fluorenone area not included) at 77% conversion:

Workup

  1. customThe reaction is monitored throughout the reaction period
  2. customby collecting samples
  3. customconsumed within 2 hours
  4. custom77% consumed within 4.5 hours

Sources & evidence

ORD record
ord-dc99462ba39c4471bf453ba53cec33db
Source dataset
uspto-grants-1999_08
Patent number
US05939494

Reaction notes

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