Dimethylformamide → HCID 12361516, compound

HRID 2420266Notes

Reaction equation

HRID 2420266 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:35](I)[CH3:36]>O>[CH2:35]([O:22][C:21]([C:19]1[O:20][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][CH:18]=1)=[O:23])[CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1151755-(Tetradecyloxy)-2-furoic acid

Product 1

HCID 12361516HCID 12361516, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 10.0 g (0.031 mole) of 5-tetradecyloxy-2-furoic acid, 4.3 g (0.034 mole) of potassium carbonate, and dimethyl formamide is stirred at room temperature after which 15.6 g (0.10 mole) of ethyl iodide is added. The mixture is heated to 50° C with stirring overnight then poured into water and extracted with ether. The ether layer is washed with water and salt water then dried over sodium sulfate, filtered, and the ether is distilled off and replaced by ethanol. Upon cooling the ethanol solution a solid is obtained which is 5-tetradecyloxy-2-furoic acid ethyl eseter, M.P. 39°-40° C.

Workup

  1. additionis added
  2. extractionextracted with ether
  3. washThe ether layer is washed with water and salt water
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. distillationthe ether is distilled off
  7. temperatureUpon cooling the ethanol solution a solid
  8. customis obtained which

Sources & evidence

ORD record
ord-41d6c9589f634bf9ba15f87cb44bb584
Source dataset
uspto-grants-1978_08
Patent number
US04110351

Reaction notes

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