Sodium Hydroxide → HCID 19046533, compound

HRID 1781487Notes

Reaction equation

HRID 1781487 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[CH3:3].[OH-].[Na+]>CO.O>[CH3:15][CH:13]([C:6]1[CH:7]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:5]=1[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH3:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86749250HCID 86749250, compound

Product 1

HCID 19046533HCID 19046533, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-[2,4,6-Tris(1-methylethyl)phenyl]propionic acid, methyl ester (2.12 g, 7.3 mmol) was dissolved in 100 mL methanol and 10 mL water. Sodium hydroxide (0.32 g, 8.0 mmol) was added and the resulting solution was stirred at room temperature for 4 hours. Concentrated in vacuo and partitioned the residue between water and diethyl ether. The aqueous layer was acidified with concentrated HC1 and extracted with dichloromethane. The organic extract was dried over MgSO4, filtered, and concentrated to give 1.87 g of 3-[2,4,6-tris(1-methyl-ethyl)phenyl]propionic acid as a white solid, mp 194°-196° C.

Workup

  1. concentrationConcentrated in vacuo
  2. custompartitioned the residue between water and diethyl ether
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2cb2b66397b5430594af21c6ef05e256
Source dataset
uspto-grants-1997_05
Patent number
US05633287

Reaction notes

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