Ethanol → HCID 19710330, compound

HRID 726152Notes

Reaction equation

HRID 726152 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4](C)[CH:3]=1.[H][H].[CH2:18](O)C>O.[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:7]=1[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 11117261HCID 11117261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19710330HCID 19710330, compound

Reagents, catalysts & solvents 1

HCID 86587499Platinum oxide monohydrateCatalyst

Procedure

A mixture of (E)-ethyl 3-(4-fluoro-2-methylphenyl)acrylate (32.9 g, 0.16 mol) and platinum oxide hydrate (0.5 g, EM Scientific) in 95% ethanol (125 ml) was placed on a Parr apparatus. After the appropriate amount of hydrogen was taken up, the catalyst was filtered and the filtrate was concentrated in vacuo to give 33.7 g of ethyl 3-(4-fluoro-3-methylphenyl)propionate. A 1.0 g sample was purified by chromatography on silica gel with hexanes:dichloromethane as eluent to give 0.92 g of ethyl 3-(4-fluoro-3-methylphenyl) propionate as a colourless oil: NMR (CDCl3); δ6.78-7.26 (m, 3H, Ar), 4.13 (q, 2H, CH2), 2.90 (t, 2H, CH2), 2.54 (t, 2H, CH2), 2.31 (s, 3H, CH3), 1.24 (t, 3H CH3).

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2005747923c946989f9d261956b3e7d7
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Reaction notes

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