Sulfuric Acid → HCID 19805178, compound

HRID 1681575Notes

Reaction equation

HRID 1681575 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].S(=O)(=O)(O)O.[CH2:17](O)[CH:18]=[CH2:19]>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:19][CH:18]=[CH2:17])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 681384-Hydroxy-3-methylbenzoic acid

Product 1

HCID 19805178HCID 19805178, compoundYield 92%

Conditions

Temperature
100 °C

Procedure

Into a round bottom flask there are introduced 9.5 g (62 mmoles) of 4-hydroxy-3-methylbenzoic acid and 70 ml of allyl alcohol. 1.8 ml of concentrated sulfuric acid are added and the mixture is heated at 100° C. for 8 hours. The reaction mixture is then evaporated to dryness, neutralized with sodium bicarbonate and extracted with dichloromethane. The organic phase is decanted, washed with water, dried over magnesium sulfate and evaporated. The resulting residue is purified simply by filtration over silica (eluant: dichloromethane). After evaporation of the solvents, 8.76 g (92% yield) of the expected ester whose melting point is obtained.

Workup

  1. customThe reaction mixture is then evaporated to dryness
  2. extractionextracted with dichloromethane
  3. customThe organic phase is decanted
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. filtrationThe resulting residue is purified simply by filtration over silica (eluant: dichloromethane)

Sources & evidence

ORD record
ord-f49ceea4f040488ea0b602324bb548cb
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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