Methanol → Xanthene

HRID 2208634Notes

Reaction equation

HRID 2208634 reaction equation
S(F)(O)(=O)=O.C[OH:7].CN[C:10]1[C:11](C)=[CH:12][CH:13]=[CH:14][C:15]=1[CH3:16].CN[C:20]1[C:21](C)=[CH:22][CH:23]=[CH:24][CH:25]=1>O>[CH:14]1[C:15]2[CH2:16][C:21]3[C:20](=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:7][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24603Fluorosulfuric acidHCID 691372,N-DimethylanilineHCID 136604N,2,6-trimethylaniline

Product 1

HCID 7107Xanthene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500 ml four-neck flask, 41.0 parts of a sulfofluoran compound of the following chemical formula (5), 312 parts of methanol, 6.79 parts of N-methyl-2,6-xylidine and 6.13 parts of N-methyl-o-toluidine were put and refluxed for 30 hours. The reaction solution was filtered at 60° C. to remove insoluble substances therefrom. Then, the solvent was removed under a reduced pressure, until the amount of the reaction solution reached about 70 ml. The reaction solution was poured into 200 parts of 6% hydrochloric acid. Then, 600 parts of water was added thereto and the mixture was stirred at room temperature for 30 minutes. Then, a wet cake was obtained by filtration. The wet cake was suspended in 100 parts of water and stirred at 60° C. for 2 hours. Then, the wet cake was obtained again by filtration, washed with hot water at 60° C. and then dried, thereby obtaining the xanthene-based dye A represented by the following chemical formula (6).

Workup

  1. temperaturerefluxed for 30 hours
  2. filtrationThe reaction solution was filtered at 60° C.
  3. customto remove insoluble substances
  4. customThen, the solvent was removed under a reduced pressure, until the amount of the reaction solution
  5. additionThe reaction solution was poured into 200 parts of 6% hydrochloric acid
  6. additionThen, 600 parts of water was added
  7. customThen, a wet cake was obtained by filtration
  8. stirringstirred at 60° C. for 2 hours
  9. customThen, the wet cake was obtained again by filtration
  10. washwashed with hot water at 60° C.
  11. customdried

Sources & evidence

ORD record
ord-a1440221704345c983f31393f969cbe9
Source dataset
uspto-grants-2016_06
Patent number
US09376571B2

Reaction notes

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