Toluene → HCID 21454054, compound

HRID 436284Notes

Reaction equation

HRID 436284 reaction equation
[CH3:1][C:2]1([CH3:20])[C:18]2[C:5](=[C:6]3[C:15](=[CH:16][CH:17]=2)[C:14]2[CH:13]=[CH:12][C:11]([OH:19])=[CH:10][C:9]=2[CH2:8][CH2:7]3)[CH2:4][CH2:3]1.C1(C)C=CC=CC=1.[H-].[Na+].Br[C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33]>O>[CH3:35][C:31]([O:19][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:6]([CH2:7][CH2:8][C:9]=2[CH:10]=1)=[C:5]1[C:18]([C:2]([CH3:20])([CH3:1])[CH2:3][CH2:4]1)=[CH:17][CH:16]=3)([CH3:36])[C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 749242-Bromo-2-methylpropanoic acidHCID 21454052HCID 21454052, compound

Product 1

HCID 21454054HCID 21454054, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 19 parts of 7,15,16,17-tetrahydro-17,17-dimethyl-6H-cyclopenta[ a]phenanthren-3-ol in 800 parts of toluene is added 13 parts of a 50% dispersion of sodium hydride in mineral oil. The resultant mixture is stirred and heated at the boiling point under reflux in an atmosphere of nitrogen for 1 hour, then cooled, whereupon approximately 13 parts 2-bromo-2-methylpropanoic acid is introduced. The mixture thus obtained is stirred and heated at the boiling point under reflux in a nitrogen atmosphere for 4 hours, at which point heating is discontinued. The mixture is stirred 18 hours longer at ambient temperatures, then approximately 250 parts of water is cautiously introduced. The mixture so produced is extracted with benzene. The benzene extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. Crystallization of the residue from a mixture of ether and hexane affords 2-methyl-2-[(7,15,16,17-tetrahydro-17,17-dimethyl-6H-cyclopenta[a]phenanthren-3-yl)oxy]propanoic acid melting at 167°-170°, and having the formula ##STR7##

Workup

  1. temperatureheated at the boiling point
  2. temperatureunder reflux in an atmosphere of nitrogen for 1 hour
  3. additionis introduced
  4. customThe mixture thus obtained
  5. temperatureheated at the boiling point
  6. temperatureunder reflux in a nitrogen atmosphere for 4 hours, at which point
  7. temperatureheating
  8. stirringThe mixture is stirred 18 hours longer at ambient temperatures
  9. customThe mixture so produced
  10. extractionis extracted with benzene
  11. extractionThe benzene extract
  12. washis washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationstripped of solvent by vacuum distillation
  15. customCrystallization of the residue
  16. additionfrom a mixture of ether and hexane

Sources & evidence

ORD record
ord-eb4e20e5adf64cc3ba8683e889d3139c
Source dataset
uspto-grants-1977_02
Patent number
US04008257

Reaction notes

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