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

HRID 2291430Notes

Reaction equation

HRID 2291430 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 (115 g, 0.751 mol) at 0° C. The resulting orange solution was stirred for 2 hours, then a solution of 236 g (0.626 mol) of N,N-di-(6-acetoxyhexyl)aniline (A2) 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 A3 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-5adc567f81b9431eadd6c15da9aa4e60
Source dataset
uspto-grants-1989_01
Patent number
US04796971

Reaction notes

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