Acetic Acid → p-Isopropenylphenol

HRID 1834490Notes

Reaction equation

HRID 1834490 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2].C([O:14][C:15](=[O:17])[CH3:16])(=O)C.C(O)(=[O:20])C>>[CH3:8][C:7]([CH2:6][C:5]([CH2:16][C:15]([OH:14])=[O:17])=[O:20])=[O:10].[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 584247p-Isopropenylphenol

Product 2

HCID 584247p-IsopropenylphenolHCID 54598443,5-Dioxohexanoic acid

Procedure

402 g (1.25 mols) of trimeric p-isopropenyl phenol are dissolved under nitrogen in 1500 g (14.5 mols) of acetic acid anhydride, followed by the addition of 25 g of the catalyst described in Example 1.1. The reaction begins with a slight heat effect under which the temperature of the reaction mixture rises to around 50° C and then falls again. When the temperature has fallen to around 30° C, the reaction mixture is heated very slowly until finally acetic acid distils off under normal pressure. The temperature of the reaction mixture is regulated in such a way that the acetic acid distils over continuously. When no more acetic acid distils off, the reaction mixture is cooled and the catalyst filtered off under suction. The remaining acetic acid and excess acetic acid anhydride are distilled off from the filtrate in a water jet vacuum and the residue left distilled in high vacuum. The triacetate of trimeric p-isopropenyl phenol is obtained in the form of a highly viscous oil in the boiling range from 250° to 254° C/0.3 Torr: yield 681 g (86% of the theoretical).

Workup

  1. customrises to around 50° C
  2. customhas fallen to around 30° C
  3. customdistils off under normal pressure
  4. customdistils over continuously
  5. customWhen no more acetic acid distils off
  6. temperaturethe reaction mixture is cooled
  7. filtrationthe catalyst filtered off under suction
  8. distillationThe remaining acetic acid and excess acetic acid anhydride are distilled off from the filtrate in a water jet vacuum
  9. waitthe residue left
  10. distillationdistilled in high vacuum

Sources & evidence

ORD record
ord-666602c6c4ce4f72b16a45ef751bd4e7
Source dataset
uspto-grants-1978_01
Patent number
US04070392

Reaction notes

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