Dimethylformamide → HCID 15729806, compound

HRID 1904554Notes

Reaction equation

HRID 1904554 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH3:12])([CH3:11])[CH:7]=[C:8]([CH3:10])[O:9][C:4]=2[CH:3]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.[OH-].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:1][C:2]2[CH:14]=[CH:13][C:5]3[C:6]([CH3:11])([CH3:12])[CH:7]=[C:8]([CH3:10])[O:9][C:4]=3[CH:3]=2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 12760922HCID 12760922, compound

Product 1

HCID 15729806HCID 15729806, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

One hundred grams of 7-hydroxy-2,4,4-trimethyl-4H-1-benzopyran (synthesized by the method of Japanese Laid-Open Patent Publication No. 5475/1981), 79 g of p-chloronitrobenzene, 42 g of potassium hydroxide, 500 ml of N,N-dimethylformamide and 500 ml of toluene were introduced into a flask equipped with the Dean-Stark condenser, and heated at 110° to 116° C. While removing the distilled water as an azeotrope with toluene, the mixture was stirred for 2 hours. The reaction mixture was cooled to room temperature, and 1 liter of water, 500 ml of ethyl acetate and 120 ml of 2N-HCl were added. The insoluble materials were separated by filtration. The filtrate was subjected to oil-water separation. The oil layer was washed with 500 ml of brine, and dried over magnesium sulfate. The solvent was evaporated. Methanol (650 ml) was added to the residue, and crystals that precipitated were collected, washed with 650 ml of hexane, and dried to give 106 g (yield 67%) of the desired product as a brown powder (melting point 80° C.).

Workup

  1. customequipped with the Dean-Stark condenser
  2. temperatureheated at 110° to 116° C
  3. customWhile removing the distilled water as an azeotrope with toluene
  4. addition1 liter of water, 500 ml of ethyl acetate and 120 ml of 2N-HCl were added
  5. customThe insoluble materials were separated by filtration
  6. customThe filtrate was subjected to oil-water separation
  7. washThe oil layer was washed with 500 ml of brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. additionMethanol (650 ml) was added to the residue, and crystals
  11. customthat precipitated
  12. customwere collected
  13. washwashed with 650 ml of hexane
  14. customdried

Sources & evidence

ORD record
ord-805b0bfd5fb649d78c6991d6ec33aead
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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