Hydrochloric Acid → HCID 20487428, compound

HRID 1702172Notes

Reaction equation

HRID 1702172 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:23]([CH3:33])[CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[C:13]([O:15]CC2C=CC=CC=2)[CH:14]=1)C1C=CC=CC=1.C(O)C.Cl.[H][H]>C(OCC)(=O)C.[Pd]>[OH:15][C:13]1[CH:12]=[C:11]([CH:23]([CH3:33])[CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:10]=[C:9]([OH:8])[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20487364HCID 20487364, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20487428HCID 20487428, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(3,5-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: 7.8 g. (80%), as an oil.

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-9c4b72c855a44133830cb4a78c1a4c5c
Source dataset
uspto-grants-1983_04
Patent number
US04380542

Reaction notes

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