Sodium Hydroxide → HCID 54574549, compound

HRID 2290934Notes

Reaction equation

HRID 2290934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=[O:9].[OH-].[Na+].[H][H]>[Ni].O>[CH3:1][O:2][C:3]1[CH2:4][CH:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 54574549HCID 54574549, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A mixture of m-methoxycinnamic acid (100 g, 0.56 mole), water (1 L), and NaOH (22.4 g, 0.56 mole), in the presence of Raney nickel catalyst (20 g, #30), was hydrogenated under 3 atmospheres H2 pressure until the theoretical uptake of hydrogen was observed. The solution was filtered, cooled to 0°, and concentrated HCl was added until acidic pH was achieved. The solid was filtered, washed with water, dried (in-vacuo) to yield 90.6 g white solid, (90%); M+ 180.

Workup

  1. filtrationThe solution was filtered
  2. temperaturecooled to 0°
  3. additionconcentrated HCl was added until acidic pH
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried (in-vacuo)

Sources & evidence

ORD record
ord-e90d795f6de345ddb4d860362f01daa2
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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