Methyl 2-(4-(4-hydroxyphenyl)cyclohexylidene)acetate → HCID 178500688, compound

HRID 632930Notes

Reaction equation

HRID 632930 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[H][H]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 58909529Methyl 2-(4-(4-hydroxyphenyl)cyclohexylidene)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 178500688HCID 178500688, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

[4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester (29 g, 0.12 mol) and 10% pd/c (2.9 g) were put into ethyl acetate and stirred under 25° C. hydrogen gas for 24 hours. The reaction mixture was filtered with celite and concentrated in the vacuum to obtain a yellow solid. The mixture was dissolved in hot ethyl acetate (29 mL) and cooled to reach ambient temperature. The reaction mixture was cooled with ice water again, a filtrate was filtered and washed with ethyl acetate (15 mL) to obtain trans [4-(4-hydroxyphenyl)cyclohexyl]acetic acid methyl ester as a white solid (12.6 g, 43%).

Workup

  1. filtrationThe reaction mixture was filtered with celite and
  2. concentrationconcentrated in the vacuum
  3. customto obtain a yellow solid
  4. temperaturecooled
  5. customto reach ambient temperature
  6. filtrationa filtrate was filtered
  7. washwashed with ethyl acetate (15 mL)

Sources & evidence

ORD record
ord-420eacedeaa146dca4ed4455519d5f88
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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