Hydrochloric Acid → 4-(3,5-Dihydroxyphenyl)-1-phenoxypentane

HRID 1995706Notes

Reaction equation

HRID 1995706 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:23]([CH3:34])=[CH:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:12]=[C:13]([O:15]CC2C=CC=CC=2)[CH:14]=1)C1C=CC=CC=1.C(O)C.Cl.[H][H]>[Pd].C(OCC)(=O)C>[OH:15][C:13]1[CH:12]=[C:11]([CH:23]([CH3:34])[CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:10]=[C:9]([OH:8])[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 544983714-(3,5-Dibenzyloxyphenyl)-1-phenoxypent-3-eneHCID 178418361HCID 178418361, compound

Product 1

HCID 204873704-(3,5-Dihydroxyphenyl)-1-phenoxypentane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3,5-dibenzyloxyphenyl)-1-phenoxypent-3-ene (51 g., 0.113M) in a mixture of absolute ethanol (160 ml.), ethyl acetate (160 ml.) and concentrated hydrochloric acid (0.2 ml.) is hydrogenated for 12 hours under 55 lbs. hydrogen in the presence of 10% Pd/C. Removal of the catalyst by filtration and concentration of the filtrate under vacuum yields 30.8 g. (100%) of product as a viscous oil.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and concentration of the filtrate under vacuum
  3. customyields 30.8 g

Sources & evidence

ORD record
ord-49fafc46ca6a458494c15ec48970efb4
Source dataset
uspto-grants-1983_09
Patent number
US04405626

Reaction notes

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