Phosphoric Acid → HCID 10457147, compound

HRID 2190899Notes

Reaction equation

HRID 2190899 reaction equation
P([O-])(O)(O)=O.[Na+].P([O-])([O-])(O)=O.[Na+].[Na+].[CH2:14]([O:21][C:22]1[C:35]2[C:34](=[O:36])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:27](=[O:45])[C:26]=2[CH:25]=[C:24]([CH2:46][OH:47])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl([O-])=[O:49].[Na+].Cl[O-].[Na+].P(=O)(O)(O)O>C(#N)C.O>[CH2:14]([O:21][C:22]1[C:35]2[C:34](=[O:36])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:27](=[O:45])[C:26]=2[CH:25]=[C:24]([C:46]([OH:49])=[O:47])[CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 6

HCID 1004Phosphoric AcidHCID 24203Sodium Phosphate, DibasicHCID 23665760Sodium HypochloriteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 46193335HCID 46193335, compound

Product 1

HCID 10457147HCID 10457147, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

10 g (0.06 moles) of radical 2,2,6,6-tetramethyl-1-piperidinyl-oxyl (TEMPO) and 1160 ml of an aqueous solution of 120 g (1 mole) of sodium dihydrogen phosphate and 180 g (1 mole) of disodium hydrogen phosphate are added in sequence to a suspension of 333 g (0.74 moles) of 1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone in 1660 ml of acetonitrile. The reaction mixture is heated to 35° C. and a solution of 167 g (1.5 moles) of sodium chlorite 80% in 513 ml of water is added dropwise in 40-50 minutes, maintaining the temperature around 35-40° C. 20 ml of aqueous sodium hypochlorite 10-12% are then dripped in and the reaction is heated to 60-65° C. for three hours. It is cooled to room temperature and 1400 ml of water are added. Phosphoric acid 85% is dripped in until reaching a pH of 2.8-3.2. The solid obtained is filtered and washed with water (350 ml×2). The damp product is dried at 50° C. at reduced pressure for 14-16 hours, providing 337 g (yield 98%) of crude dibenzylrhein.

Workup

  1. temperaturemaintaining the temperature around 35-40° C
  2. temperatureis heated to 60-65° C. for three hours
  3. temperatureIt is cooled to room temperature
  4. customThe solid obtained
  5. filtrationis filtered
  6. washwashed with water (350 ml×2)
  7. customThe damp product is dried at 50° C. at reduced pressure for 14-16 hours
  8. customproviding 337 g (yield 98%) of crude dibenzylrhein

Sources & evidence

ORD record
ord-7c7e38ab63e947479fcd7c3f26e87702
Source dataset
uspto-grants-2012_12
Patent number
US08324411B2

Reaction notes

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