Sulfuric Acid → HCID 13561781, compound

HRID 1380369Notes

Reaction equation

HRID 1380369 reaction equation
N[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:21]>O>[OH:21][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13561779HCID 13561779, compound

Product 1

HCID 13561781HCID 13561781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diazonium salt was prepared by the same way as in Example 6 using 6.47 grams of 4-(7-amino-2-fluorenyl)-butan-2-one. The diazonium salt was dropped into a refluxing and stirring mixture of 9 ml of concentrated sulphuric acid and 150 ml of water. After being stirred for 2 hours, the mixture was cooled and crystals separated out therefrom were collected by filtration. They were washed until the washing became neutral and dried with air. The resulting crystals were subjected to a silica gel column chromatography, eluted with a 4:1 mixture of n-hexane and ethyl acetate, and the resulting crystals were recrystallized from methanol to give 4.96 grams of 4-(7-hydroxy-2-fluorenyl)-butan-2one, pale yellow crystals, m.p. 170°-170.5° C.

Workup

  1. stirringAfter being stirred for 2 hours
  2. temperaturethe mixture was cooled
  3. customcrystals separated out
  4. filtrationtherefrom were collected by filtration
  5. washThey were washed until the washing
  6. customdried with air
  7. washeluted with a 4:1 mixture of n-hexane and ethyl acetate
  8. customthe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-4198e8301d93447bab7072d94f0ad624
Source dataset
uspto-grants-1986_04
Patent number
US04581377

Reaction notes

Loading…