Ethylene Glycol → HCID 20343286, compound

HRID 1447916Notes

Reaction equation

HRID 1447916 reaction equation
[OH-:1].[Na+].[CH:3]([CH:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:21])([F:20])[CH:17]([F:19])[F:18])=[CH:11][CH:10]=1)[C:7]#N)([CH3:5])[CH3:4].C(O)C[OH:24]>>[CH3:4][CH:3]([CH3:5])[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:21])([F:20])[CH:17]([F:19])[F:18])=[CH:11][CH:10]=1)[C:7]([OH:24])=[O:1]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 20343306HCID 20343306, compound

Product 1

HCID 20343286HCID 20343286, compoundYield 89%

Conditions

Temperature
135 °C

Procedure

A stirred mixture of 48.0 g (24.0 g real, 0.60 mol) of 50% sodium hydroxide, 21.78 g (0.0791 mol) of α-isopropyl-p-(1,1,2,2-tetrafluoroethoxy)phenylacetonitrile, and 240 ml of ethylene glycol is heated at 135° C. for 12 hours. After dilution with 600 ml of water the reaction mixture is washed twice with 100 ml of ether. The water layer is acidified with concentrated hydrochloric acid and then extracted twice with 300 ml of ether. The ether solution is washed twice with 500 ml of water, dried with sodium sulfate, filtered, and then evaporated to give 20.74 g (89%) of a brown solid, melting point 92° C. to 97° C. (hexane).

Workup

  1. washAfter dilution with 600 ml of water the reaction mixture is washed twice with 100 ml of ether
  2. extractionextracted twice with 300 ml of ether
  3. washThe ether solution is washed twice with 500 ml of water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-467be234a33245c091ce7b4e6371f390
Source dataset
uspto-grants-1979_12
Patent number
US04178460

Reaction notes

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