Sodium Hydroxide → HCID 19046533, compound

HRID 2396292Notes

Reaction equation

HRID 2396292 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 layerwas acidified with concentrated HCl and extracted with dichloromethane. Theorganic extract was dried over MgSO4, filtered, and concentrated to give 1.87 g of 3-[2,4,6-tris(1-methylethyl)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. dry with materialTheorganic extract was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e18ef52cd254b3dbf8877f9d8278b99
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

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