Ethanol → Ethyl 3-(4-chlorophenyl)-2,2-dimethylpropanoate

HRID 1646429Notes

Reaction equation

HRID 1646429 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[CH2:13]([OH:15])C.F.[C]=[O:18].CCCC[CH2:23][CH3:24]>[Cr].[Co]>[CH3:10][C:9]([CH3:11])([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:13]([O:15][CH2:23][CH3:24])=[O:18]

Participants

7

Reactant 5

HCID 702EthanolHCID 8058HexaneHCID 14917Hydrofluoric Acid2×HCID 202426Benzenemethanol, 4-chloro-alpha-(1-methylethyl)-HCID 178418416HCID 178418416, compound

Product 1

HCID 12373578Ethyl 3-(4-chlorophenyl)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 11332432Hastelloy CCatalyst

Conditions

Temperature
-30 °C

Procedure

1-(4'-Chlorophenyl)-2-methyl-1-propanol (9.6 grams, 0.05 moles), ethanol (4.5 grams, 0.1 mole), and hexane (32 grams) are charged into a 300 cubic centimeter Hastelloy C autoclave. The autoclave is purged twice with nitrogen, evacuated to 100 mm Hg, and cooled to -30° C. Hydrogen fluoride (75 grams, 3.25 mole) is then added and the reactor is pressurized to 600 psig with carbon monoxide. The reaction mass is stirred for about an hour at room temperature. The hydrogen fluoride is vented and the contents are removed and poured onto crushed ice. A solution of 45% potassium hydroxide is added to the mixture until the pH of the mixture is adjusted to 6.0-6.5. The mixture is then extracted with ethyl acetate (3 times with 150 ml of ethyl acetate each time). The combined organic extract is dried with anhydrous magnesium sulfate, filtered, and concentrated to yield the crude product. The crude product is distilled under vacuum to give pure ethyl 2,2-dimethyl-3-(4'-chlorophenyl)propanoate.

Workup

  1. customThe autoclave is purged twice with nitrogen
  2. customevacuated to 100 mm Hg
  3. customthe contents are removed
  4. additionpoured
  5. customonto crushed ice
  6. additionA solution of 45% potassium hydroxide is added to the mixture until the pH of the mixture
  7. extractionThe mixture is then extracted with ethyl acetate (3 times with 150 ml of ethyl acetate each time)
  8. extractionThe combined organic extract
  9. dry with materialis dried with anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto yield the crude product
  13. distillationThe crude product is distilled under vacuum

Sources & evidence

ORD record
ord-4b0dbf58f1b3417681ace3e3d80539f9
Source dataset
uspto-grants-1993_01
Patent number
US05179229

Reaction notes

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