Diisopropylethylamine → 3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid

HRID 2240769Notes

Reaction equation

HRID 2240769 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[C:5]([CH3:15])[CH:4]=1)=[O:2].CCN(C(C)C)C(C)C>C(O)C.[Pd]>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:5]([CH3:15])[CH:4]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 765393083-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid

Product 1

HCID 574374033-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acidYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid (2.2 g, 10.8 mmol) and DIPEA (2.0 mL, 11.9 mmol) in ethanol (80 mL), Pd/C (200 mg, 10% Pd, moistened with 50% water) is added. The suspension is vigorously stirred under 1 bar of H2 for 1 h. The mixture is filtered over Celite and the filtrate is evaporated. The residue is poured onto 1 N aq. HCl/ice and extracted with EA. The organic extract is washed once with 1 N aq. HCl and once with brine, dried over MgSO4, filtered and evaporated to give 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (2.2 g) as a pale yellow resin; LC-MS: tR=0.71 min.

Workup

  1. filtrationThe mixture is filtered over Celite
  2. customthe filtrate is evaporated
  3. additionThe residue is poured onto 1 N aq. HCl/ice
  4. extractionextracted with EA
  5. extractionThe organic extract
  6. washis washed once with 1 N aq. HCl and once with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-1733b5c4407c49fdb9ac1b8b6f177181
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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