Diisopropylethylamine → 3-(2-Ethyl-4-hydroxymethyl-6-methyl-phenyl)propionic acid

HRID 2240779Notes

Reaction equation

HRID 2240779 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[C:5]([CH3:11])[C:4]=1[CH:12]=[CH:13][C:14]([OH:16])=[O:15])[CH3:2].CCN(C(C)C)C(C)C>C(O)C.[Pd]>[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[C:5]([CH3:11])[C:4]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:2]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

Product 1

HCID 574374133-(2-Ethyl-4-hydroxymethyl-6-methyl-phenyl)propionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (2.75 g, 12.6 mmol) and DIPEA (1.8 g, 13.8 mmol) in ethanol (80 mL), Pd/C (275 mg, 10% Pd, moistened with 50% water) is added. The mixture is stirred for 16 h at rt under 1 atm of H2. The catalyst is filtered off and the filtrate is concentrated. The residue is dissolved in EA, washed with 2 N aq. HCl, followed by 1 N aq. HCl and brine. The organic extract is dried over Na2SO4, filtered and evaporated to give 3-(2-ethyl-4-hydroxymethyl-6-methyl-phenyl)-propionic acid (2.8 g) as a white solid; LC-MS: tR=0.76 min.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in EA
  4. washwashed with 2 N aq. HCl
  5. extractionThe organic extract
  6. dry with materialis dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9a663e46ba654a4680f25e216930e31a
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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