Acetic Acid → 4-butoxy-2-fluorobenzoic acid

HRID 466499Notes

Reaction equation

HRID 466499 reaction equation
S(=O)(=O)(O)O.O.[CH2:7]([O:11][C:12]1[CH:19]=[CH:18]C(C#N)=[C:14]([F:20])[CH:13]=1)[CH2:8][CH2:9][CH3:10].[C:21]([OH:24])(=[O:23])[CH3:22]>>[CH2:7]([O:11][C:12]1[CH:19]=[CH:18][C:22]([C:21]([OH:24])=[O:23])=[C:14]([F:20])[CH:13]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 19010186HCID 19010186, compound

Product 1

HCID 27734344-butoxy-2-fluorobenzoic acid

Procedure

A mixture of concentrated sulphuric acid (190 ml) and water (190 ml) was added dropwise to a stirred solution of compound 18 (19.0 g, 0.098 mol) in glacial acetic acid (380 ml). The stirred mixture was heated under reflux for 48 h, cooled in a refrigerator for 24 h and the product was filtered off and dried (CaCl2) in vacuo to give pale-yellow crystals.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 48 h
  3. temperaturecooled in a refrigerator for 24 h
  4. filtrationthe product was filtered off
  5. dry with materialdried (CaCl2) in vacuo
  6. customto give pale-yellow crystals

Sources & evidence

ORD record
ord-b8fa157587a542b48347c288fc4b79cc
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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