Sulfuric Acid → Allyl 4-hydroxy-3-tert.butylbenzoate

HRID 1681577Notes

Reaction equation

HRID 1681577 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([CH3:14])([CH3:13])[CH3:12].[CH2:15](O)[CH:16]=[CH2:17].S(=O)(=O)(O)O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:17][CH:16]=[CH2:15])=[O:7])=[CH:4][C:3]=1[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 144015103-tert-Butyl-4-hydroxybenzoic acid

Product 1

HCID 19805158Allyl 4-hydroxy-3-tert.butylbenzoateYield 83%

Conditions

Temperature
100 °C

Procedure

Into a round bottom flask, there are introduced 9.71 g (50 mmoles) of 4-hydroxy-3-tert.butyl benzoic acid and 55 ml of allyl alcohol. 1.3 ml of concentrated sulfuric acid are added and the mixture in heated at 100° C. for 18 hours. The reaction mixture is then evaporated to dryness and 200 ml of water are added. The mixture is then neutralized with sodium bicarbonate and extracted with ethyl ether. The organic phase is decanted, washed with water, dried over magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column by eluting with dichloromethane. After evaporation of the solvents, 9.78 g (83% yield) of the expected ester whose melting point is 131°-132° C. are obtained.

Workup

  1. customThe reaction mixture is then evaporated to dryness and 200 ml of water
  2. additionare added
  3. extractionextracted with ethyl ether
  4. customThe organic phase is decanted
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe resulting residue is purified by chromatography on a silica column
  9. washby eluting with dichloromethane

Sources & evidence

ORD record
ord-d92a36d9e6564a789ea001e5e37bdd87
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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