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

HRID 2396290Notes

Reaction equation

HRID 2396290 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 theresidue 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 1.33g 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
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e50f2cb825134ed3b9c67c90aa71c3d0
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

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