Hydrochloric Acid → Ethyl (4-acetylphenyl)acetate

HRID 1184964Notes

Reaction equation

HRID 1184964 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:17](Cl)(=[O:19])[CH3:18].Cl>C(=S)=S>[C:17]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2][CH:3]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7590Ethyl phenylacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 73716Ethyl (4-acetylphenyl)acetateYield 21.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of ethyl 2-phenylacetate (A-1) (50.9 g, 305 mmol) in CS2 (220 mL) was added AlCl3 (93.6 g, 702 mmol) at 0˜10° C. over 10 min. After addition, acetyl chloride (30.5 mL, 427 mmol) was added at 0˜10° C. over 10 min. After addition, the reaction mixture was slowly heated to reflux overnight, then poured into ice-cooled 5N HCl solution (600 mL), extracted with EA (200 mL×3). The combined organic phase was washed with water (200 mL), sat. NaHCO3 (200 mL) and brine (200 mL), dried over Na2SO4, concentrated to afford a brown oil. Recrystallized with PE/acetone (150 mL/20 mL) in refrigerator to afford A-2 as a yellow crystal solid (13.8 g, 19%).

Workup

  1. additionwas added at 0˜10° C. over 10 min
  2. additionAfter addition
  3. temperaturethe reaction mixture was slowly heated
  4. temperatureto reflux overnight
  5. additionpoured into ice-
  6. extractionextracted with EA (200 mL×3)
  7. washThe combined organic phase was washed with water (200 mL), sat. NaHCO3 (200 mL) and brine (200 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customto afford a brown oil
  11. customRecrystallized with PE/acetone (150 mL/20 mL) in refrigerator

Sources & evidence

ORD record
ord-66251c5e982a4d6386f954d591fe229a
Source dataset
uspto-grants-2014_03
Patent number
US08669381B2

Reaction notes

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