Dimethylformamide → Hydroxytetradecane Ether

HRID 1760052Notes

Reaction equation

HRID 1760052 reaction equation
[OH-].[Na+].[O:3]1[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4]1.[CH3:18]N(C)C=O>C1(C)C=CC=CC=1>[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH3:6][CH2:5][O:3][CH2:4][CH3:18]

Participants

5

Reactant 3

HCID 6228Dimethylformamide3×HCID 14798Sodium HydroxideHCID 186041,2-Epoxytetradecane

Product 1

HCID 87205352Hydroxytetradecane Ether

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

15.0 g (0.035 mol) of the polyerythritol prepared in Example 1 and 0.15 g of sodium hydroxide were dissolved in 20 ml of N,N-dimethylformamide while heating at 150° C. in a dried nitrogen gas flow, and stirred for 30 minutes. 14.8 g (0.070 mol) of 1,2-epoxytetradecane in 50 ml of N,N-dimethylformamide was added to the mixture, which was further stirred for four hours at 105° C. in a dried nitrogen gas flow. After the reaction, N,N-dimetylformamide was evaporated to obtain adcrude product. After dissolving the crude product in 100 ml of hot toluene and cooling the solution to room temperature, unreacted polyerythritol was filtered out. The toluene in the filtrate was evaporated in vaccuo to obtain 28.5 g of a white powdery desired product.

Workup

  1. stirringwas further stirred for four hours at 105° C. in a dried nitrogen gas flow
  2. customwas evaporated
  3. customto obtain adcrude product
  4. temperaturecooling the solution to room temperature
  5. filtrationunreacted polyerythritol was filtered out
  6. customThe toluene in the filtrate was evaporated in vaccuo

Sources & evidence

ORD record
ord-448d1fad38044f098b84c61bdd5a2c44
Source dataset
uspto-grants-2005_01
Patent number
US06838544B2

Reaction notes

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