Hydrochloric Acid → HCID 20337487, compound

HRID 1706266Notes

Reaction equation

HRID 1706266 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][C:10]=1[CH:23]([CH3:33])[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)C1C=CC=CC=1.C(O)C.Cl.[H][H]>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH:23]([CH3:33])[CH2:24][CH2:25][O:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20337428HCID 20337428, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20337487HCID 20337487, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(2,5-dibenzyloxyphenyl)-1-phenoxybutane (14.7 g., 133.5 mM) in a mixture of ethyl acetate (110 ml.), ethanol (110 ml.) and concentrated hydrochloric acid (0.7 ml.) is hydrogenated for 2 hours under 60 p.s.i. hydrogen in the presence of 10% palladium-on-carbon (1.5 g.). Removal of the catalyst by filtration and concentration of the filtrate gives an oil. The oil is purified by chromatography on silica gel (100 g.) and eluting with benzene-ethyl acetate consisting of 0-10% ethyl acetate. The middle fractions are combined and concentrated to give the title product.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and concentration of the filtrate
  3. customgives an oil
  4. customThe oil is purified by chromatography on silica gel (100 g.)
  5. washeluting with benzene-ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c596cb94c2544ad39d72a3462266cc84
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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