Water → HCID 70233539, compound

HRID 1089843Notes

Reaction equation

HRID 1089843 reaction equation
C[C:2]1([CH3:20])[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](O)=O)=[C:4]([C:17](O)=O)[CH2:3]1.[OH2:21]>>[CH3:7][C:6]1[CH:20]=[CH:2][C:3](=[O:21])[C:4]2[C:5]=1[C:8]1[C:16](=[CH:15][CH:14]=[CH:13][C:9]=1[CH3:10])[CH:17]=2

Participants

3

Reactant 2

HCID 962WaterHCID 131717138HCID 131717138, compound

Product 1

HCID 70233539HCID 70233539, compound

Conditions

Temperature
60 °C

Procedure

4,4-Dimethyldiphenic acid (20.0 g, 74.0 mmol) was charged with polyphosphoric acid (83.4 g) at room temperature. The mixture was heated in an oil bath at 120°-121° C. for 6.5 hr until decarboxylation was over (no gas evolved). The reaction mixture was cooled down to 60° C., diluted with water (150 mL) then cooled down to room temperature. The precipitate was filtered off, washed with water, 10% sodium bicarbonate solution until the filtrate became colorless, extracted with 25% solution of ethyl acetate in hexane and dried over magnesium sulfate. Evaporation of the solvents gave the crude ketone which was purified by short path chromatography (5% ethyl acetate in hexane). This afforded 10.8 g (70.4%) of 4,5-dimethylfluorenone.

Workup

  1. temperatureThe mixture was heated in an oil bath at 120°-121° C. for 6.5 hr until decarboxylation
  2. temperaturethen cooled down to room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with water, 10% sodium bicarbonate solution until the filtrate
  5. extractionextracted with 25% solution of ethyl acetate in hexane
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvents

Sources & evidence

ORD record
ord-03ab3507b57a4291b35a18c42bdf9267
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

Loading…