Hydrochloric Acid → 3-(3,4-Dihydroxy-5-nitrophenyl)-1-(4-methylphenyl)prop-2-en-1-one

HRID 1195955Notes

Reaction equation

HRID 1195955 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.O[C:15]1[C:20]([N+]([O-])=O)=[CH:19][C:18]([C:24](=[O:26])[CH3:25])=[CH:17][C:16]=1OC.[CH3:29]CC(C1C=CC=CC=1)=O.Cl>O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:25][C:24]([C:18]2[CH:19]=[CH:20][C:15]([CH3:29])=[CH:16][CH:17]=2)=[O:26])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71481-Phenyl-1-propanoneHCID 2947641-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanoneHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 539899903-(3,4-Dihydroxy-5-nitrophenyl)-1-(4-methylphenyl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 5.49 g of 3,4-dihydroxy-5-nitrobenzaldehyde and 5.37 g of 4,-methylacetophenone in 50 ml of tetrahydrofuran was added a catalytic amount of gaseous hydrogen chloride and refluxed for 4.5 h. The solvent was evaporated in vacuo and the residue crystallized from ether-petroleum-ether, yield 1.85 g (21%), m.p. 184°-186° C.

Workup

  1. temperaturerefluxed for 4.5 h
  2. customThe solvent was evaporated in vacuo
  3. customthe residue crystallized from ether-petroleum-ether, yield 1.85 g (21%), m.p. 184°-186° C.

Sources & evidence

ORD record
ord-0a1415816a7c4d128fab40b22bc537a9
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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