Triethylene Glycol → HCID 21524265, compound

HRID 917915Notes

Reaction equation

HRID 917915 reaction equation
[CH3:1][C:2]1([C:19]([OH:21])=[O:20])[C:11]2[C:6](=[CH:7][C:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.O.NN.[OH-].[K+].C(O)COCCOCCO>>[CH3:1][C:2]1([C:19]([OH:21])=[O:20])[C:11]2[C:6](=[CH:7][C:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 8172Triethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21524257HCID 21524257, compound

Product 1

HCID 21524265HCID 21524265, compound

Conditions

Temperature
195 °C

Procedure

A mixture of 12 g of l-methyl-4-oxo-6-cyclohexyl-1,2,3,4-tetrahydronaphthalene-1 -carboxylic acid, 10 g of hydrazine hydrate, 13.7 g of potassium hydroxide, and 85 ml of triethylene glycol is heated at 130°-140°C for 2 hours. After that, while distilling off a mixture of hydrazine and water, the temperature is raised up to 195°C, and the batch is stirred until the evolution of nitrogen ceases. The mixture is then diluted with 50 ml of water, acidified with concentrated hydrochloric acid, then extracted with ethyl acetate. The resin-like crude product remaining after evaporation of the ethyl acetate is crystallized from toluene and yields 1-methyl-6-cyclohexyl-1,2,3,4-tetrahydronaphthalene-1carboxylic acid of the formula ##SPC12##

Workup

  1. temperatureis heated at 130°-140°C for 2 hours
  2. distillationAfter that, while distilling off
  3. additiona mixture of hydrazine and water
  4. additionThe mixture is then diluted with 50 ml of water
  5. extractionextracted with ethyl acetate
  6. customafter evaporation of the ethyl acetate
  7. customis crystallized from toluene

Sources & evidence

ORD record
ord-e22b80126362400cb2777cfed897a76d
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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