Acetic Acid → 2,3-Dihydro-2,4-dimethyl-7-nitrobenzofuran

HRID 279890Notes

Reaction equation

HRID 279890 reaction equation
[CH2:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[OH:14])[CH:2]=[CH2:3].C(O)(=O)C.Br>CCOCC>[CH3:3][CH:2]1[CH2:1][C:4]2[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=2[O:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 135756673-Methyl-6-nitro-2-(prop-2-en-1-yl)phenol

Product 1

HCID 135756682,3-Dihydro-2,4-dimethyl-7-nitrobenzofuran

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

47 g of 1B was added to a mixture of 100 ml of glacial acetic acid and 100 ml of 48% aqueous hydrobromic acid and the mixture was heated at 114°-115° C. for 2.5 hours. The resulting mixture was stripped to dryness, the residue was taken up in 500 ml of ether, and filtered. The filtrate was concentrated to 100 ml, 300 ml of hexane was added, the mixture was chilled and filtered to give 2,3-dihydro-2,4-dimethyl-7-nitrobenzofuran (1C), as a tan solid, m.p.: 69°-71° C.

Workup

  1. temperaturethe mixture was heated at 114°-115° C. for 2.5 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to 100 ml, 300 ml of hexane
  4. additionwas added
  5. temperaturethe mixture was chilled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-322d2b48fe654f38ab93095f0d344369
Source dataset
uspto-grants-1986_05
Patent number
US04587259

Reaction notes

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