4-tert-Butylphenol → Butyl 3-(p-tert-butylphenoxy)-propionate

HRID 544592

Reaction equation

HRID 544592 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:14]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:17])[CH:15]=[CH2:16]>C1(NC2C=CC3C(=CC=CC=3)C=2)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:16][CH2:15][C:14]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 8846Butyl AcrylateHCID 24758Sodium hydride

Product 1

HCID 14423333Butyl 3-(p-tert-butylphenoxy)-propionateYield 45.2%

Reagents, catalysts & solvents 1

HCID 8679N-phenyl-2-naphthylamineCatalyst

Procedure

A solution of 25 g (0.167 mole) p-tert-butylphenol, 0.2 g sodium hydride (as 50% dispersion in oil), 0.2 g N-phenyl-2-naphthylamine (as basic polymerization inhibitor) in 75.0 g (0.586 mole) butyl acrylate was heated at 125° C. for four hours. The temperature was then reduced to 100° C. and the excess acrylate distilled under gentle vacuum. The resulting oil was filtered through 900 g silica gel (90 to 200 mesh) using chloroform as eluant to yield 21.0 g pure butyl 3-(p-tert-butyl-phenoxy)-propionate (45%).

Workup

  1. customwas then reduced to 100° C.
  2. distillationthe excess acrylate distilled under gentle vacuum
  3. filtrationThe resulting oil was filtered through 900 g silica gel (90 to 200 mesh)

Sources & evidence

ORD record
ord-35bc94f231fd4189a8a1d4929278d303
Source dataset
uspto-grants-1984_05
Patent number
US04451474

Linked notes

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