Sodium Hydroxide → 3-[2,4,6-Tris-(1-methylethyl)phenyl]-2-propenyl carboxylic acid

HRID 1781485Notes

Reaction equation

HRID 1781485 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:15]([CH3:17])[CH3:16])[C:7]=1[CH:18]=[CH:19][CH2:20][C:21]([O:23]C)=[O:22])[CH3:5]>CO.O>[CH3:5][CH:4]([C:6]1[CH:11]=[C:10]([CH:12]([CH3:13])[CH3:14])[CH:9]=[C:8]([CH:15]([CH3:16])[CH3:17])[C:7]=1[CH:18]=[CH:19][CH2:20][C:21]([OH:23])=[O:22])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 867492493-[2,4,6-Tris(1-methylethyl)phenyl]-2-propenyl carboxylic acid, methyl ester

Product 1

HCID 538822253-[2,4,6-Tris-(1-methylethyl)phenyl]-2-propenyl carboxylic acidYield 88.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (0.23 g, 5.7 mmol) was added to a solution of 3-[2,4,6-tris (1-methylethyl)phenyl]-2-propenyl carboxylic acid, methyl ester (1.5 g, 5.2 mmol) in 100 mL methanol and 10 mL water. Stirred at room temperature for 48 hours and concentrated to dryness. Partitioned the residue between water and diethyl ether. The aqueous layer was acidified with concentrated HCl and extracted with dichloromethane. The organic extract was dried over MgSO4, filtered, and concentrated to give 1.33 g of 3-[2,4,6-tris-(1-methylethyl)phenyl]-2-propenyl carboxylic acid as a white solid, mp 201°-203° C.

Workup

  1. concentrationconcentrated to dryness
  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-31bb48e3aefa493c969c0a88c7fc3f77
Source dataset
uspto-grants-1997_05
Patent number
US05633287

Reaction notes

Loading…