Hydrochloric Acid → HCID 53917946, compound

HRID 430658Notes

Reaction equation

HRID 430658 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([C:10]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=2[CH:12]=O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-].[CH3:23][O:24][CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.Cl>C1(C)C=CC=CC=1>[CH3:23][O:24][CH:25]=[CH:12][C:11]1[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:10]=1[C:8](=[O:9])[C:7]1[CH:20]=[CH:21][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 158394314-Methoxy-2-(4-nitrobenzoyl)benzaldehyde

Product 1

HCID 53917946HCID 53917946, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g of 2-(4-nitrobenzoyl)-4-methoxybenzaldehyde is introduced together with 18 g of (methoxymethyl)triphenylphosphonium chloride in 400 ml of toluene and mixed in portions with 5.9 g of potassium-tert-butylate while being cooled with ice. After 1 hour of stirring while being cooled with ice and a subsequent 3.5 hours of stirring at room temperature, it is mixed with 200 ml of water, weakly acidified with 1N hydrochloric acid and extracted three times with ethyl acetate. The ethyl acetate phases are washed with saturated common salt solution, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with hexane:ethyl acetate=1:1 as an eluant. 6.9 g of 1-methoxy-2-(4-methoxy-2-(4-nitrobenzoyl)phenyl)ethylene as a mixture of the E- and Z-forms is obtained.

Workup

  1. temperaturewhile being cooled with ice
  2. temperaturewhile being cooled with ice and a subsequent 3.5 hours
  3. stirringof stirring at room temperature
  4. extractionextracted three times with ethyl acetate
  5. washThe ethyl acetate phases are washed with saturated common salt solution
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed on silica gel with hexane
  10. addition6.9 g of 1-methoxy-2-(4-methoxy-2-(4-nitrobenzoyl)phenyl)ethylene as a mixture of the E-
  11. customZ-forms is obtained

Sources & evidence

ORD record
ord-5ea26593c34a47e2bbab182ef2368c73
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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