N,N-Dimethylaniline → HCID 86708419, compound

HRID 921481Notes

Reaction equation

HRID 921481 reaction equation
[CH2:1]([O:10][CH2:11][C:12]([CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH2:15][CH3:16])[CH2:13][OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].CN(C)C1C=CC=CC=1.O1CCCC1.[C:42](Cl)(=[O:52])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>O>[CH2:19]([O:18][CH2:17][C:12]([CH2:11][O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])([CH2:15][CH3:16])[CH2:13][O:14][C:42](=[O:52])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8028TetrahydrofuranHCID 66982Decanoyl chlorideHCID 86708418HCID 86708418, compound

Product 1

HCID 86708419HCID 86708419, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1-L three-neck flask provided with a stirrer, thermometer, condenser and dropping funnel with a gas inlet tube, 73.4 g (0.19 mol) of 2,2-bis(nonyloxymethyl)butane-1-ol, 26.7 g (0.22 mol) of N,N-dimethylaniline and 150 mL of tetrahydrofuran were put, to which 38.1 g (0.2 mol) of decanoyl chloride was dropped and stirred at the room temperature under nitrogen stream. After the dropping, the mixture was heated to 45 degrees C. and stirred for five hours. After the reaction, a small amount of distilled water was added to the mixture to dissolve the generated white solid. The mixture was transferred to a separating funnel. After an aqueous layer was separated while an organic layer was added with 50 mL of tetrahydrofuran, washed with 200 mL of saturated saline and with 20 mL of dilute sulfuric acid and then washed with distilled water until the organic layer became neutral. The obtained organic layer was dried with magnesium sulfate. After the solvent was removed by an evaporator, 100 g of the mixture was subjected to vacuum distillation to be fractioned. The obtained fraction was subjected to mass analysis, NMR analysis and IR analysis, whereby the fraction was confirmed to be an ester (target compound) (mass analysis result: m/z=540). The obtained amount was 61.8 g (0.114 mol) (a yield of 60%).

Workup

  1. customTo a 1-L three-neck flask provided with a stirrer
  2. customthermometer, condenser and dropping
  3. additionwas dropped
  4. temperatureAfter the dropping, the mixture was heated to 45 degrees C
  5. stirringand stirred for five hours
  6. customAfter the reaction
  7. dissolutionto dissolve the generated white solid
  8. customThe mixture was transferred to a separating funnel
  9. customAfter an aqueous layer was separated while an organic layer
  10. additionwas added with 50 mL of tetrahydrofuran
  11. washwashed with 200 mL of saturated saline and with 20 mL of dilute sulfuric acid
  12. washwashed with distilled water until the organic layer
  13. dry with materialThe obtained organic layer was dried with magnesium sulfate
  14. customAfter the solvent was removed by an evaporator, 100 g of the mixture
  15. distillationwas subjected to vacuum distillation

Sources & evidence

ORD record
ord-0078ca496be940c88bccf10d00dcde84
Source dataset
uspto-grants-2016_03
Patent number
US09273264B2

Reaction notes

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