3-(3'-Hydroxyphenyl)propionic acid → HCID 22557021, compound

HRID 983789Notes

Reaction equation

HRID 983789 reaction equation
[H][H].[OH:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([OH:14])=O)[CH:7]=[CH:8][CH:9]=1.[OH-:15].[Na+].[OH2:17].[CH:18](Cl)(Cl)Cl>>[CH:18]([C:9]1[CH:8]=[CH:7][C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:17])=[CH:5][C:4]=1[OH:3])=[O:15]

Participants

6

Reactant 5

HCID 913-(3'-Hydroxyphenyl)propionic acidHCID 962WaterHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 178418361HCID 178418361, compound

Product 1

HCID 22557021HCID 22557021, compound

Conditions

Temperature
70 °C

Procedure

Scheme IX illustrates the preparation of aldehydes 21. For example, a compound of formula 20 wherein R3, R4 and R5 are hydrogen, i.e., 3-(3-hydroxyphenyl)propionic acid, (3.0 g, 0.018 mol, Aldrich Chemical Comp, Cat 1279), NaOH (6 g, 0.15 mol), water (40 mL), and chloroform (40 ml) were combined and heated at 70° C. for 12 h in a 100 ml round bottom flask. The solution is acidified to pH 4, extracted with EtOAc (2×30 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to give 3-(4-formyl-3-hydroxy phenyl)propionic acid which was used without further purification.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c4f26857ad84369b61dc16c4aa657e4
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

Loading…