Hydrochloric Acid → HCID 22002658, compound

HRID 1940141Notes

Reaction equation

HRID 1940141 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:16].[Na+].Cl>C(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[OH:16][C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22002634Cyclopentyl[4-(methylsulfanyl)phenyl]methanone

Product 1

HCID 22002658HCID 22002658, compoundYield 69.9%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of the ketone from Step 1 (7.2 g, 32.7 mmol) in 4.7 ml CCl4 and 9.6 ml toluene was added Aliquat 336 (2.11 g, 5.20 mmol) and powdered NaOH (2.88 g, 71.9 mmol) and the mixture was stirred for 16 h at r.t. To the brown mixture was added 100 ml of 5% aq. HCl and extracted with EtOAc (4×100 ml). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (20% EtOAc/hexane) gave 5.4 g of the title compound as a white waxy solid (70%).

Workup

  1. extractionextracted with EtOAc (4×100 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e79a3a28d7234b3c8df2a9206023a1e5
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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