Acetic Anhydride → HCID 735605, compound

HRID 1650626Notes

Reaction equation

HRID 1650626 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.C(OC(=O)C)(=O)C>O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[CH:17][C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 735605HCID 735605, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The photo-bleachable compound expressed by the structural formula (II-14) was prepared in the following manner. Thus, a reaction mixture was prepared by dissolving 6.81 g (0.05 mole) of p-anisaldehyde and 4.66 g (0.05 mole) of γ-picoline in 10.21 g (0.10 mole) of acetic anhydride and the mixture was heated under reflux for 16 hours to effect the reaction. After acetic acid and the unreacted acetic anhydride were evaporated from the reaction mixture, the residual reaction mixture was poured into water so that a crystalline material was precipitated therein. The reaction mixture was filtered and the collected precipitates were washed with water. Recrystallization of the precipitates from a mixture of methyl alcohol and water gave 5.80 g of 4-[2-(4-methoxyphenyl)ethenyl]pyridine, the yield of which was 55% of the theoretical value.

Workup

  1. customwas prepared in the following manner
  2. customThus, a reaction mixture was prepared
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 16 hours
  5. customthe reaction
  6. customAfter acetic acid and the unreacted acetic anhydride were evaporated from the reaction mixture
  7. customthe residual reaction mixture
  8. customwas precipitated
  9. filtrationThe reaction mixture was filtered
  10. customthe collected precipitates
  11. washwere washed with water
  12. customRecrystallization of the
  13. customprecipitates from a mixture of methyl alcohol and water

Sources & evidence

ORD record
ord-e236daba85914e95812c101844e4c896
Source dataset
uspto-grants-1990_05
Patent number
US04925770

Reaction notes

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