Butyl phenyl ether → HCID 20507056, compound

HRID 354665

Reaction equation

HRID 354665 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH2:22])[CH:10]=[C:11](S([O-])(=O)=O)[C:12]=3[OH:17])[C:7](=[O:23])[C:6]=2[C:5]([OH:24])=[C:4](S([O-])(=O)=O)[CH:3]=1.[Na+].[Na+].[CH2:31]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:32][CH2:33][CH3:34]>B(O)(O)O.S(=O)(=O)(O)O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH2:22])[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:23])[C:6]=2[C:5]([OH:24])=[CH:4][C:3]=1[C:39]1[CH:40]=[CH:41][C:36]([O:35][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 14311Butyl phenyl etherHCID 72278C.I. Acid Blue 45

Product 1

HCID 20507056HCID 20507056, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 7628Boric AcidSolvent

Conditions

Temperature
80 °C

Procedure

4.0 g of sodium 4,8-diamino-1,5-dihydroxy-anthraquinone-2,6-disulfonate is dissolved in a mixture of 2.0 g of boric acid and 30 ml concentrated sulphuric acid heated to 80° C. The blue solution obtained is cooled to a temperature of 0° to 5° C., and 2.8 g of butoxybenzene is stirred in drop by drop, the colour then changing from blue to reddish brown. The mixture is agitated for a further two hours at 0° to 10° C., then poured onto ice. The suspension obtained is heated on reflux for 4 hours to destroy the boric ester, and a violet precipitate is filtered off after cooling, corresponding to 4,8-diamino-1,5-dihydroxy-3-p-butoxyphenyl-anthraquinone-6-sulphonic acid. The moist precipitate is dissolved hot in a mixture of 24 ml of 33% ammonia and 160 ml of water, and the sulphonic groups are separated by adding 2.2 g of sodium dithionate in stages. The mixture is finally heated to 95° C. for approximately 2 hours, then cooled and filtered. The precipitate thus obtained is washed with slightly acidified water, then with a great excess of water, and dried. The desired product may further be purified by crystallisation or chromatography if necessary.

Workup

  1. customThe blue solution obtained
  2. stirringThe mixture is agitated for a further two hours at 0° to 10° C.
  3. additionpoured onto ice
  4. customThe suspension obtained
  5. temperatureis heated
  6. temperatureon reflux for 4 hours
  7. customto destroy the boric ester
  8. filtrationa violet precipitate is filtered off
  9. temperatureafter cooling, corresponding to 4,8-diamino-1,5-dihydroxy-3-p-butoxyphenyl-anthraquinone-6-sulphonic acid
  10. dissolutionThe moist precipitate is dissolved hot in a mixture of 24 ml of 33% ammonia and 160 ml of water
  11. customthe sulphonic groups are separated
  12. additionby adding 2.2 g of sodium dithionate in stages
  13. temperatureThe mixture is finally heated to 95° C. for approximately 2 hours
  14. temperaturecooled
  15. filtrationfiltered
  16. customThe precipitate thus obtained
  17. washis washed with slightly acidified water
  18. dry with materialwith a great excess of water, and dried
  19. customThe desired product may further be purified by crystallisation or chromatography if necessary

Sources & evidence

ORD record
ord-7545972047e24fd28517b881a9d21b05
Source dataset
uspto-grants-1983_03
Patent number
US04376715

Linked notes

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