HCID 21406503, compound → (+-)-Cicloprofen

HRID 1729895Notes

Reaction equation

HRID 1729895 reaction equation
[CH2:1]=[C:2]([C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]=2[CH:7]=1)[C:3]([OH:5])=[O:4]>O1CCOCC1.[Pd]>[CH3:1][CH:2]([C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]=2[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 21406503HCID 21406503, compound

Product 1

HCID 37589(+-)-CicloprofenYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of α-methylenefluorene-2-acetic acid (2.6g.) in dioxane (50ml.) is hydrogenated in the presence of 5% palladium on charcoal (800mg.). The mixture is filtered and the filtrate evaporated to dryness. The residue is sublimed to afford the title compound (2.6g.). The analytical sample is prepared by recrystallization from aqueous methanol, mp 180°-182°.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-63827fc808b24e46b2f27f96477644f4
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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