Phosphorus oxychloride → [(4-Formylphenyl)azanediyl]di(hexane-6,1-diyl) diacetate

HRID 414438Notes

Reaction equation

HRID 414438 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:8])[CH3:7].[C:33]([O-])(=[O:35])C.[Na+]>CN(C)C=O>[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])[C:17]1[CH:18]=[CH:19][C:20]([CH:33]=[O:35])=[CH:21][CH:22]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 21278581HCID 21278581, compound

Product 1

HCID 21278577[(4-Formylphenyl)azanediyl]di(hexane-6,1-diyl) diacetateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N-Dimethylformamide (DMF, 250 mL) was added dropwise with stirring under nitrogen to phosphorous oxychloride at 0° C. The resulting orange solution was stirred for 2 hours, then a solution of 236 g (0163 mol) of N,N-di-(6-acetoxyhexyl)aniline in 250 mL of DMF was added slowly. The reaction mixture was stirred under nitrogen for 1 hour at 0° C. and then for 6 hours at 80° C. After cooling, the solution was poured onto 500 g of ice plus 200 g of sodium acetate, and the resulting mixture was extracted with dichloromethane (4×250 mL). The combined organic extracts were washed four times with 250 mL portions of water, dried over anhydrous sodium sulfate, and then concentrated at reduced pressure to produce a light brown oil. The oil was fractionally distilled in vacuo to yield 192 g (76%) of the title compound as a gold oil, bp 220°-260° C. (0.007 mm).

Workup

  1. stirringThe reaction mixture was stirred under nitrogen for 1 hour at 0° C.
  2. waitfor 6 hours at 80° C
  3. temperatureAfter cooling
  4. extractionthe resulting mixture was extracted with dichloromethane (4×250 mL)
  5. washThe combined organic extracts were washed four times with 250 mL portions of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customto produce a light brown oil
  9. distillationThe oil was fractionally distilled in vacuo

Sources & evidence

ORD record
ord-a2d7d794a898467185b87265e942d096
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

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