Sulfuric Acid → Guaiacylacetone

HRID 426465Notes

Reaction equation

HRID 426465 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13](O)[CH:14]([OH:16])[CH3:15])=[CH:9][C:8]=1[O:18][CH3:19]>C1(C)C=CC=CC=1>[CH3:15][C:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[C:8]([O:18][CH3:19])[CH:9]=1)=[O:16]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14524462HCID 14524462, compound

Product 1

HCID 17262Guaiacylacetone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a refluxing azeotropic mixture of 125 ml toluene and 100 ml 10% sulfuric acid is added an aqueous solution (~250 ml.) to 9.0 g 1-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol (from step C) at such a rate that the volume of the aqueous phase remained constant during the addition, returning the toluene and separating the aqueous phase of the distillate by a Dean-Stark head. The separation of the water is discontinued after ~250 ml is collected and the reaction mixture is refluxed for an additional hour.

Workup

  1. additionremained constant during the addition
  2. customseparating the aqueous phase of the distillate by a Dean-Stark head
  3. customThe separation of the water
  4. customis collected
  5. temperaturethe reaction mixture is refluxed for an additional hour

Sources & evidence

ORD record
ord-74116eb3f00c4f7b83df3f4b4698ece0
Source dataset
uspto-grants-1979_10
Patent number
US04169858

Reaction notes

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