Ethanol → 3-Chloro-4,5-dipropargyloxybenzoic acid

HRID 1608128Notes

Reaction equation

HRID 1608128 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:32][CH2:33][C:34]#[CH:35])[C:27]=1[O:28][CH2:29][C:30]#[CH:31])[CH:23]=[O:24].C(O)C>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:32][CH2:33][C:34]#[CH:35])[C:27]=1[O:28][CH2:29][C:30]#[CH:31])[C:23]([OH:3])=[O:24]

Participants

7

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 141303053-Chloro-4,5-dipropargyloxybenzaldehydeHCID 131709961Jones' reagent

Product 1

HCID 141303193-Chloro-4,5-dipropargyloxybenzoic acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

Jones reagent (e.g. an aqueous sulfuric acid solution of chromium trioxide) was added to a solution of 3-chloro-4,5-dipropargyloxybenzaldehyde (18.0 g) in acetone (100 ml) under stirring at a temperature below 20° C. The addition was stopped when the reaction mixture became red, and stirring was continued at 20° C. for 1 hour. The reaction mixture was poured into ice-water containing ethanol (100 nl) and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane to give 3-chloro-4,5-dipropargyloxybenzoic acid (16.2 g). m.p. 158°-159° C.

Workup

  1. additionThe addition
  2. stirringstirring
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-29ce923a91004e6caa86109a79a52d68
Source dataset
uspto-grants-1989_09
Patent number
US04870064

Reaction notes

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