Hydrochloric Acid → HCID 14715323, compound

HRID 1885780Notes

Reaction equation

HRID 1885780 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][C:6](=[C:9]2[CH2:14][CH2:13][CH:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.Cl.O>O1CCCC1.[Cl-].[Na+].O>[CH:15]1([CH:12]2[CH2:13][CH2:14][C:9](=[C:6]3[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]3)[CH2:10][CH2:11]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 18952706HCID 18952706, compound

Product 1

HCID 14715323HCID 14715323, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-(4'-cyclohexylcyclohexylidene)cyclohexanone dimethyl ketal (0.016 mol) and 1.0N HCl (100 ml) in tetrahydrofuran (125 ml) was left at room temperature for 2.5 hours at which time TLC indicated hydrolysis to be complete. Water and brine were added to the reaction solution and the mixture was extracted with ether (4×). The pooled ether extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to give 4.49 g of white solid. This solid was chromatographed (790 g of 40-63 μm silica gel, 4.5 l of 5% ethyl acetate-hexane followed by 10% ethyl acetate-hexane) with 4-(4'-cyclohexylcyclohexylidene)cyclohexanone dimethyl ketal (0.56 g, 10%) eluted first followed by the title compound. Recrystallization of the title compound from hexane gave colorless crystals, mp 81°-81.5° C.

Workup

  1. customhydrolysis
  2. extractionthe mixture was extracted with ether (4×)
  3. washThe pooled ether extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-12259249000d4d5b9590727f09ec1768
Source dataset
uspto-grants-1992_09
Patent number
US05145874

Reaction notes

Loading…