Acetic Acid → HCID 15671152, compound

HRID 2351516Notes

Reaction equation

HRID 2351516 reaction equation
C([O:8][C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13](=[O:32])[CH2:14][C:15]([CH3:31])([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl.C(O)(=O)C>O>[OH:8][C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13](=[O:32])[CH2:14][C:15]([CH3:31])([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[O:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15671125HCID 15671125, compound

Product 1

HCID 15671152HCID 15671152, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13.5 g or 7-benzyloxy-2,8-dimethyl-2-(4-nitrophenoxymethyl)-4-oxochroman (prepared as described in Preparation 15, 40 ml of concentrated aqueous hydrochloric acid and 80 ml of acetic acid was heated under reflux for 3 hours. At the end of this time, the reaction mixture was poured into water and extracted with benzene. The benzene solution was washed with water and then dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. Cyclohexane was added to the residue to crystallize it. 9.55 g of the title compound were obtained as a pale red powdery substance.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. extractionextracted with benzene
  5. washThe benzene solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. additionCyclohexane was added to the residue
  9. customto crystallize it

Sources & evidence

ORD record
ord-1f29bde4be6f42058dfa0df84d6f62d1
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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