Hydrochloric Acid → HCID 15729800, compound

HRID 1904556Notes

Reaction equation

HRID 1904556 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[CH:21]=[CH:20][C:12]3[C:13]([CH3:19])([CH3:18])[CH:14]=[C:15]([CH3:17])[O:16][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[OH-:25].[Na+]>C(OCC)(=O)C.O.CC(C)=O>[OH:25][C:15]1([CH3:17])[CH2:14][C:13]([CH3:19])([CH3:18])[C:12]2[CH:20]=[CH:21][C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:23][CH:22]=3)=[CH:10][C:11]=2[O:16]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15729806HCID 15729806, compound

Product 1

HCID 15729800HCID 15729800, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6.5 g of the 7-(4-nitrophenoxy)-2,4,4-trimethyl-4H-1-benzopyran, 26 ml of water, 13 ml of conc. hydrochloric acid and 65 ml of acetone was refluxed for 2 hours. An 10% aqueous solution of sodium hydroxide was added to the reaction mixture to neutralize it, and then 100 ml of water and 200 ml of ethyl acetate were added, and the mixture was subjected to oil-water separation. The oil layer was washed with 50 ml of brine, dried over magnesium sulfate and concentrated. Toluene (5 ml) and 45 ml of hexane was added to the residue, and the precipitated crystals were collected by filtration, washed with 50 ml of hexane and dried to give 5.1 g (yield 70%) of a pale brown powder (mp. 159°-160° C., recrystallized from ethanol).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe mixture was subjected to oil-water separation
  3. washThe oil layer was washed with 50 ml of brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. additionToluene (5 ml) and 45 ml of hexane was added to the residue
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with 50 ml of hexane
  9. customdried

Sources & evidence

ORD record
ord-131b57c8761f4f6f818f756b06d760d3
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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