Hydrochloric Acid → HCID 67460426, compound

HRID 554528Notes

Reaction equation

HRID 554528 reaction equation
Cl.C([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1)O)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>[OH-].[Pd+2].[OH-].CO.C(OCC)(=O)C>[CH3:27][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[OH:9])=[CH:19][CH:20]=1)(=[O:25])=[O:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67458638HCID 67458638, compound

Product 1

HCID 67460426HCID 67460426, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a nitrogen stream, a 20% palladium hydroxide catalyst (299 mg) and 36% HCl (150 μL, 1.78 mmol) were added to a solution of (2-benzyloxyphenyl)-(4-methane-sulfonylphenyl)methanol (3.00 g, 8.14 mmol) in a mixture of methanol (30 mL) and ethyl acetate (30 mL), and the mixture was stirred under a hydrogen atmosphere for six hours. To the reaction mixture was added sodium hydrogencarbonate and the mixture was stirred for 30 minutes to be neutralized, and then the catalyst was filtered off. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:2)] to obtain the title compound (1.81 g, 85%).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationthe catalyst was filtered off
  3. distillationThe solvent was distilled under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:2)]

Sources & evidence

ORD record
ord-d411b2b30a72461baa73ec89ef5bf05b
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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