4-Nitrophenol → 6-nitro-3,4-dihydro-2H-1-benzopyran-4-one

HRID 981786Notes

Reaction equation

HRID 981786 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[C:11](O)(=[O:14])[CH:12]=[CH2:13].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.F>>[N+:7]([C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[O:10][CH2:13][CH2:12][C:11]2=[O:14])([O-:9])=[O:8]

Participants

5

Reactant 4

HCID 9804-NitrophenolHCID 6581Acrylic AcidHCID 7108PhenothiazineHCID 14917Hydrofluoric Acid

Product 1

HCID 52288316-nitro-3,4-dihydro-2H-1-benzopyran-4-one

Procedure

Following the same procedure as Example 1, p-nitrophenol (34.8 grams), acrylic acid (27 grams), and an inhibitor, phenothiazine (0.02 grams) was added to the pressure reactor. The anhydrous hydrogen fluoride (110 grams) was added before the system was warmed. When the reaction temperature was attained, a pressure of 140 psig was noted, similar to previous reactions. Work-up was carried out as previous examples and the 6-Nitro-4-Chromanone was isolated and characterized.

Workup

  1. temperaturewas warmed

Sources & evidence

ORD record
ord-da5d1197fd644d779e21cbae81c0ff80
Source dataset
uspto-grants-1991_02
Patent number
US04992564

Reaction notes

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