Water → Fluoreneone

HRID 1585772Notes

Reaction equation

HRID 1585772 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.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

5

Reactant 4

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

Product 1

HCID 22281833Fluoreneone

Conditions

Temperature
45 °C

Procedure

9-Fluorenone (6.44 g, 0.0358 mol, 1.00 equiv.), molten phenol (70.0 g, 0.744 mol, 20.8 equiv.), and deionized water (1.93 g, 0.107 mol, 3.00 equiv.) is added to the reactor (reactor design 3). The reaction mixture is heated to 45° C. with stirring under a pad of nitrogen. 3-Mercaptopropanesulfonic acid (0.385 g, 2.47 mmol, 0.0690 equiv.) is added slowly over approximately 1 minute to the reaction mixture at 45° C. The reaction is monitored throughout the reaction period by collecting samples and analyzing by HPLC. The 9-fluorenone is found to be 4% consumed within 9 minutes, 13% consumed within 1 hour, 29% consumed within 3.5 hours, and 94% consumed within 20.5 hours. HPLC analysis (analytical method 3) gives the following relative area % analysis for the reaction products (fluorenone area not included) at 94% conversion:

Workup

  1. customThe reaction is monitored throughout the reaction period
  2. customby collecting samples
  3. customconsumed within 9 minutes
  4. custom13% consumed within 1 hour
  5. custom29% consumed within 3.5 hours
  6. custom94% consumed within 20.5 hours

Sources & evidence

ORD record
ord-8aaa69fc7d934718a0d1ec3b778dd54e
Source dataset
uspto-grants-1999_08
Patent number
US05939494

Reaction notes

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