Sulfuric Acid → Allyl 3-fluoro-4-hydroxybenzoate

HRID 1729524Notes

Reaction equation

HRID 1729524 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:17](O)[CH:18]=[CH2:19]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH2:19][CH:18]=[CH2:17])=[O:6]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 14852487Allyl 3-fluoro-4-hydroxybenzoateYield 55%

Conditions

Temperature
100 °C

Procedure

Into a round bottom flask, there are introduced 5.35 g (35 mmoles) of 3-fluoro-4-hydroxybenzoic acid and 50 ml of allyl alcohol. 1.5 ml of concentrated sulfuric acid are added and the mixture is heated to 100° C. for 12 hours. The reaction medium is evaporated to dryness and 200 ml of water are added. The reaction medium is neutralized with sodium bicarbonate and extracted with dichloromethane. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a silica column by eluting with an 80:20 mixture of dichloromethane and hexane. 3.7 g (55% yield) of the expected ester having a melting point of 42°-43° C. are recovered.

Workup

  1. customThe reaction medium is evaporated to dryness and 200 ml of water
  2. additionare added
  3. extractionextracted with dichloromethane
  4. customThe organic phase is decanted
  5. washwashed with water
  6. customdried on magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a silica column
  10. washby eluting with an 80:20 mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-baa9b1356c9f41448a1d7b81eafd4d52
Source dataset
uspto-grants-1994_07
Patent number
US05332856

Reaction notes

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