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

HRID 1958773Notes

Reaction equation

HRID 1958773 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) was added. The mixture was stirred for 16 h at rt under 1 atm of H2. The catalyst was filtered off and the filtrate was concentrated. The residue was dissolved in EA and washed with 2 N aq. HCl, followed by 1 N aq. HCl and brine. The org. extract was dried over Na2SO4, filtered and evaporated to give 3-(2-ethyl-4-hydroxymethyl-6-methyl-phenyl)-propionic acid as a white solid (2.8 g). LC-MS: tR=0.76 min.

Workup

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

Sources & evidence

ORD record
ord-7f9630c7b0ff4612821ed9b0596a3629
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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