3-[4-(Benzyloxy)-3-chlorophenyl]-1-cyclopentylpropan-1-one → 3-(3-Chloro-4-hydroxyphenyl)-1-cyclopentylpropan-1-one

HRID 858739Notes

Reaction equation

HRID 858739 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:11][C:10]=1[Cl:24])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[Cl:24][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][C:17]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 587627613-[4-(Benzyloxy)-3-chlorophenyl]-1-cyclopentylpropan-1-one

Product 1

HCID 587626963-(3-Chloro-4-hydroxyphenyl)-1-cyclopentylpropan-1-oneYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(benzyloxy)-3-chlorophenyl]-1-cyclopentylpropan-1-one (48 g, 0.140 mole), from Step 1, and 10% palladium-on-carbon (11.52 g of 50 wt % wet, 0.005 mol, 3.5 mole %) in ethyl acetate (500 mL) was degassed and purged with hydrogen three times. The reaction was stirred with 1 atm H2 for 4 h, resulting in complete conversion. The mixture was filtered through a fine fritted glass funnel and the filtrate concentrated in vacuo, affording a yellow oil which crystallized on cooling. This material was recrystallized from two parts of isopropyl ether, affording 22 g (62%) of the title product. mp 88–90° C.

Workup

  1. custompurged with hydrogen three times
  2. customresulting in complete conversion
  3. filtrationThe mixture was filtered through a fine fritted glass funnel
  4. concentrationthe filtrate concentrated in vacuo
  5. customaffording a yellow oil which
  6. customcrystallized
  7. temperatureon cooling
  8. customThis material was recrystallized from two parts of isopropyl ether

Sources & evidence

ORD record
ord-f630553557d34b0c896e595408d3523a
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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