Phenol, 3-cyclohexyl- → HCID 21447331, compound

HRID 597269Notes

Reaction equation

HRID 597269 reaction equation
[H-].[Na+].[CH:3]1([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C([O:18][C:19](=[O:23])[CH:20](Br)[CH3:21])C>O1CCCC1>[CH:3]1([C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[O:15][CH:20]([CH3:21])[C:19]([OH:23])=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 16036Phenol, 3-cyclohexyl-HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 21447331HCID 21447331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

11 g of a 55% oily sodium hydride dispersion are deoiled with petroleum ether in an atmosphere of nitrogen, and 500 cc of dry tetrahydrofuran are then added. 44 g of 3 -cyclohexyl-phenol in 500 cc of dry tetrahydrofuran are added dropwise within approximately 30 minutes while stirring. 46 g of 2-bromopropionic acid ethyl ester are then added dropwise while stirring. The reaction mixture is heated to 60° for 1 hour and is then allowed to stand at room temperature for 16 hours. The reaction mixture is concentrated by evaporation and the residue is divided thrice between methylene chloride and water. The aqueous phases are again extracted twice with methylene chloride. The organic phases are combined, dried over anhydrous sodium sulphate and concentrated. The residue is boiled at reflux for 2 hours in a solution of 50 g of potassium hydroxide in 900 cc of methanol and 100 cc of water. The reaction solution is concentrated to a great extent by evaporation, acidified to pH = 2 with 2 N hydrochloric acid and extracted thrice with methylene chloride. The organic phases are washed once with water, combined, dried over anhydrous sodium sulphate and concentrated. Recrystallization of the residue from petroleum ether yields 2-(3-cyclohexyl-phenoxy)propionic acid having an M.P. of 81°-82°.

Workup

  1. additionare then added
  2. stirringwhile stirring
  3. temperatureThe reaction mixture is heated to 60° for 1 hour
  4. concentrationThe reaction mixture is concentrated by evaporation
  5. extractionThe aqueous phases are again extracted twice with methylene chloride
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. temperatureat reflux for 2 hours in a solution of 50 g of potassium hydroxide in 900 cc of methanol and 100 cc of water
  9. concentrationThe reaction solution is concentrated to a great extent by evaporation
  10. extractionextracted thrice with methylene chloride
  11. washThe organic phases are washed once with water
  12. dry with materialdried over anhydrous sodium sulphate
  13. concentrationconcentrated
  14. customRecrystallization of the residue from petroleum ether

Sources & evidence

ORD record
ord-993cc7ad5f8b456d88d8c2a20ca4e2bd
Source dataset
uspto-grants-1977_03
Patent number
US04013690

Reaction notes

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