3,4,5-Trimethoxyphenol → 2'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone

HRID 1095273

Reaction equation

HRID 1095273 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23](Cl)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[OH:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[C:4]=1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 695053,4,5-TrimethoxyphenolHCID 3194633-(4-nitrophenyl)prop-2-enoyl Chloride

Product 1

HCID 727670692'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalconeYield 22%

Conditions

Temperature
80 °C

Procedure

A mixture of 3,4,5-trimethoxyphenol (1.85 g, 10 mmol) and 4-nitrocinnamoyl chloride (2.11 g, 10 mmol) was dissolved in BF3-Et2O complex (10 ml) and heated to 80° C. for 10 min, and then quenched with excess of water. The aqueous layer was extracted with dichloromethane. The combined organic layer was concentrated and the residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3) gave 7a (0.79 g, 22%) and 7b (1.54 g, 43%). 1H NMR (400 MHz, CDCl3) μ 3.81 (s, 3H), 3.90 (s, 3H), 3.91 (s, 3H), 6.29 (s, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.76 (d, J=16.0 Hz, 1H), 8.01 (d, J=16.0 Hz, 1H), 8.26 (d, J=8.8 Hz, 2H), 13.44 (s, 1H).

Workup

  1. dissolutionwas dissolved in BF3-Et2O complex (10 ml)
  2. customquenched with excess of water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. concentrationThe combined organic layer was concentrated
  5. customthe residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3)

Sources & evidence

ORD record
ord-4049c48a3e50449dade86f120b203cfc
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Linked notes

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