Triethylene Glycol → HCID 14614335, compound

HRID 986230Notes

Reaction equation

HRID 986230 reaction equation
[C:1]1([C:7]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([CH2:12][CH2:13][C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][C:19](=O)[CH2:20][CH2:21][C:22]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][C:24]([OH:26])=[O:25])[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.[OH-].[K+].C(O)COCCOCCO>>[C:1]1([C:7]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:23][C:24]([OH:26])=[O:25])[CH2:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 8172Triethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20158445HCID 20158445, compound

Product 1

HCID 14614335HCID 14614335, compound

Conditions

Temperature
120 °C

Procedure

0.27 g. 3,3,14,14-Tetraphenyl-6,11-diketohexadecane-1,16-dioic acid, prepared according to Example 23, and 0.23 g. 85% hydrazine hydrate were added to a solution of 0.4 g. KOH in 10 ml. triethylene glycol. The mixture was heated for 24 hours at 120° C., subsequently heated to 195° C. in order to evaporate the water and then boiled under reflux for 7 hours. The mixture was cooled, diluted with water, extracted with ether, acidified and extracted with ether. The ether extract was washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness.

Workup

  1. temperaturesubsequently heated to 195° C. in order
  2. customto evaporate the water
  3. temperatureunder reflux for 7 hours
  4. temperatureThe mixture was cooled
  5. additiondiluted with water
  6. extractionextracted with ether
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. washwas washed with water
  10. dry with materialdried over anhydrous magnesium sulphate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-15ebf77083d24b7c9626170c4db02add
Source dataset
uspto-grants-1987_12
Patent number
US04711896

Reaction notes

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