Water → 10-(4,4-Diethoxybutyl)-9-acridanone

HRID 986258Notes

Reaction equation

HRID 986258 reaction equation
[H-].[Na+].[CH:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:18]([O:20][CH:21]([O:26][CH2:27][CH3:28])[CH2:22][CH2:23][CH2:24]Cl)[CH3:19].O>CN(C)C=O>[CH2:18]([O:20][CH:21]([O:26][CH2:27][CH3:28])[CH2:22][CH2:23][CH2:24][N:8]1[C:7]2[C:16](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15](=[O:17])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 2015AcridoneHCID 24758Sodium hydrideHCID 2625984-Chlorobutyraldehyde Diethyl Acetal

Product 1

HCID 1401493610-(4,4-Diethoxybutyl)-9-acridanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.44 g of sodium hydride in 100 ml of dimethylformamide is treated within 10 minutes with 9.75 g of 9-acridanone and held at 50° for 2 hours. At 120° there are then added 9.5 g of 4,4-diethoxybutyl chloride. After 16 hours, the mixture is cooled, poured into water and extracted with dichloromethane. The extract is dried over sodium sulfate and evaporated. The residue is extracted with hexane and crystallized twice from hexane. There is obtained 10-(4,4-diethoxybutyl)-9-acridanone of metling point 73°-74.5°.

Workup

  1. waitAfter 16 hours
  2. temperaturethe mixture is cooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract is dried over sodium sulfate
  5. customevaporated
  6. extractionThe residue is extracted with hexane
  7. customcrystallized twice from hexane

Sources & evidence

ORD record
ord-77992ace7d414238b18f1a599aade8be
Source dataset
uspto-grants-1987_12
Patent number
US04711889

Reaction notes

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