Water → HCID 18472389, compound

HRID 861868Notes

Reaction equation

HRID 861868 reaction equation
[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH:13]([C:18]([O:20]C)=[O:19])[C:14]3=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O>ClCCl.CO>[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13]([C:18]([OH:20])=[O:19])=[CH:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19700499Methyl 7-cyclohexyl-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate

Product 1

HCID 18472389HCID 18472389, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 7-cyclohexyl-1-tetralone-2-carboxylate (8.6 g) was dissolved in dichloromethane (40 ml)-methanol (50 ml). To this solution, sodium borohydride (1.13 g) was added in small portions at room temperature. The reaction mixture was poured into water (80 ml) and extracted with dichloromethane. The dichloromethane layer was successively washed with water and brine, and dried (MgSO4), after which the solvent was distilled off. The residual oil was dissolved in methanol (40 ml), followed by dropwise addition of 2N NaOH (45 ml) at room temperature and stirring for 1 hour. The reaction mixture was washed with ether; the aqueous layer was acidified with concentrated hydrochloric acid and extracted with dichloromethane. The dichloromethane layer was successively washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off. To the residual oil, dioxane (25 ml) and concentrated hydrochloric acid (4.2 ml) were added, followed by stirring at 90° C. for 40 minutes, after which the mixture was concentrated under reduced pressure. After water was added, the residue was extracted with ethyl acetate. The ethyl acetate layer was successively washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off, to yield 7-cyclohexyl-3,4-dihydronaphthalene-2-carboxylic acid (1.57 g, 20%), which was then recrystallized from ethanol to yield colorless prisms having a melting point of 179°-180° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was successively washed with water and brine
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. dissolutionThe residual oil was dissolved in methanol (40 ml)
  6. additionfollowed by dropwise addition of 2N NaOH (45 ml) at room temperature
  7. washThe reaction mixture was washed with ether
  8. extractionextracted with dichloromethane
  9. washThe dichloromethane layer was successively washed with water and brine
  10. dry with materialdried (MgSO4)
  11. customafter which the solvent was evaporated off
  12. additionTo the residual oil, dioxane (25 ml) and concentrated hydrochloric acid (4.2 ml) were added
  13. stirringby stirring at 90° C. for 40 minutes
  14. concentrationafter which the mixture was concentrated under reduced pressure
  15. additionAfter water was added
  16. extractionthe residue was extracted with ethyl acetate
  17. washThe ethyl acetate layer was successively washed with water and brine
  18. dry with materialdried (MgSO4)
  19. customafter which the solvent was evaporated off

Sources & evidence

ORD record
ord-05ee07620db24609bc3ade72e6b4e51e
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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