Toluene → 3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propionic acid allyl ester

HRID 2059123Notes

Reaction equation

HRID 2059123 reaction equation
[NH2-].[Li+].[CH2:3]([OH:6])[CH:4]=[CH2:5].C[O:8][C:9](=O)[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:15]([OH:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]=1.C1(C)C=CC=CC=1>C(O)(=O)C>[CH2:3]([O:6][C:9](=[O:8])[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:19])([CH3:21])[CH3:20])[C:15]([OH:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]=1)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7858Allyl AlcoholHCID 24532Lithium amideHCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Product 1

HCID 205457203-(3,5-Di-t-butyl-4-hydroxyphenyl)-propionic acid allyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

0.2 g of lithium amide and in the course of 5 hours 38 g of allyl alcohol are added at 150° C. under nitrogen to 146 g of 3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionic acid methyl ester. After completion of the addition, stirring is maintained at 150° C. for a further 10 hours. The brownish reaction mixture is cooled to about 100° C., and 150 ml of toluene, 0.5 g of concentrated acetic acid and 10 g of "Celite Hyflow Supercel" (product of Johns Manville Corp., USA) are added. There is thus obtained, after filtration and then removal of the solvent in vacuo, the title compound in crystalline form, m.p. about 40° C.

Workup

  1. additionAfter completion of the addition
  2. customThe brownish reaction mixture
  3. temperatureis cooled to about 100° C.
  4. customThere is thus obtained
  5. filtrationafter filtration
  6. customremoval of the solvent in vacuo

Sources & evidence

ORD record
ord-504d49677280405fba3127a71044c487
Source dataset
uspto-grants-1982_03
Patent number
US04322303

Reaction notes

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