Benzene → Ethyl (4-chlorophenyl)acetate

HRID 1090808Notes

Reaction equation

HRID 1090808 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12](O)[CH3:13].C1C=CC=CC=1>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 241BenzeneHCID 702EthanolHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 84177Ethyl (4-chlorophenyl)acetateYield 97%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

To p-chlorophenylacetic acid (85.30 g, 0.50 mole) was added ethanol (92 g, 2.0 mole), benzene (78.11 g) and conc. sulfuric acid (2.5 g, 0.025 mole) and the azeotropic dehydration reaction was performed for 6 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, while it was cool and the solution was extracted with diethyl ether. The ether layer was dried with anhydrous sodium sulfate, diethyl ether was distilled off under reduced pressure and the resulting residue was distilled under reduced pressure to give 96.30 g (96.9%) of the title compound as a colorless liquid, b.p. 105°-106° C./2.5 mmHg (lit. 130° C./13 mmHg).

Workup

  1. customthe azeotropic dehydration reaction
  2. additionwas added to the reaction mixture, while it
  3. temperaturewas cool
  4. extractionthe solution was extracted with diethyl ether
  5. dry with materialThe ether layer was dried with anhydrous sodium sulfate, diethyl ether
  6. distillationwas distilled off under reduced pressure
  7. distillationthe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-51db630e34a249e09162b15fea4cc60f
Source dataset
uspto-grants-1992_01
Patent number
US05082947

Reaction notes

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