{4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid → HCID 178525564, compound

HRID 585709Notes

Reaction equation

HRID 585709 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=[CH:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1>[Pd].C(O)C>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 9942924{4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid

Product 1

HCID 178525564HCID 178525564, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added {4-[2,4-dihydroxyphenyl]cyclohexylidene}acetic acid (50 mg, 0.20 mmol) and ethanol (15 ml). To the stirred solution was added palladium (catalytic amount, 10% on activated carbon) in one portion. The reaction vessel was evacuated and then placed under an atmosphere of hydrogen. This was repeated ten times and then stirred for 17 hr under a hydrogen atmosphere at room temperature. The reaction mixture was filtered through a celite plug, washing with ethanol. The solvent was removed in vacuo to give the title compound (50 mg, 100%) as a pale yellow oil. m/z (ES+) 251 (M+H+); δH(CD3OD) 1.33-1.91 (9H, m), 2.30 (2H, m), 2.81 (1H, m), 6.28 (2H, m), 6.94 (1H, m).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. customThe reaction vessel was evacuated
  3. filtrationThe reaction mixture was filtered through a celite plug
  4. washwashing with ethanol
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-444600d5699948a3b8bf5c608b7bab04
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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