Ethylene Glycol → 5-Chloro-6-cyclohexyl-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 1415328Notes

Reaction equation

HRID 1415328 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)C(C=NO)[CH2:8][CH2:7]2.[CH2:22]([OH:25])[CH2:23]O>>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH:23]([C:22]([OH:25])=[O:1])[CH2:8][CH2:7]2

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 86733087HCID 86733087, compound

Product 1

HCID 214844735-Chloro-6-cyclohexyl-2,3-dihydro-1H-indene-1-carboxylic acid

Conditions

Temperature
190 °C

Procedure

600 mg of finely powdered potassium hydroxide are added to a suspension of 500 mg of crude 5-chloro-6-cyclohexyl-indane-1-aldoxime in 20 ml of ethylene glycol and the mixture is stirred for 3 hours at 190° C under nitrogen. It is then cooled to room temperature and the reaction mixture is partitioned between 50 ml of ether and 50 ml of water. The aqueous layer is twice washed with 50 ml of ether at a time. The organic phases are extracted with 50 ml of water and the aqueous phases are adjusted to pH 2 with concentrated hydrochloric acid and extracted twice, with 50 ml of methylene chloride at a time. The methylene chloride phases are washed until neutral, dried over sodium sulphate and evaporated to dryness in vacuo. Chromatography of the evaporation residue on 20 g of silica gel, with benzene/ethyl acetate/glacial acetic acid (80:20:1) as the eluting agent, yields pure 5-chloro-6-cyclohexyl-1-indanecarboxylic acid of melting point 140°-143° C (from petroleum ether).

Workup

  1. temperatureIt is then cooled to room temperature
  2. customthe reaction mixture is partitioned between 50 ml of ether and 50 ml of water
  3. washThe aqueous layer is twice washed with 50 ml of ether at a time
  4. extractionThe organic phases are extracted with 50 ml of water
  5. extractionextracted twice, with 50 ml of methylene chloride at a time
  6. washThe methylene chloride phases are washed until neutral,
  7. dry with materialdried over sodium sulphate
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4f16db710ac1430e8e5c6cd48071929d
Source dataset
uspto-grants-1977_01
Patent number
US04004026

Reaction notes

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