Ethanol → Ethyl (4-chlorophenyl)acetate

HRID 1192339Notes

Reaction equation

HRID 1192339 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]>S(=O)(=O)(O)O>[CH2:12]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH3:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 84177Ethyl (4-chlorophenyl)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

The (4-chlorophenyl)-acetic acid (20.0 g, 106 mmol) was dissolved in 220 mL of ethanol at ambient temperature. A catalytic amount of sulfuric acid (10 drops) was added to afford a light yellow solution. The reaction was allowed to stir overnight to completion and was concentrated to 30 mL. The concentrate was partitioned between ethyl acetate and half-saturated NaHCO3 solution. The aqueous was extracted with ethyl acetate, and the organics were combined. The organic was washed with water, brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired pure (4-chlorophenyl)-acetic acid ethyl ester as a pale yellow oil (21.0 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 7.29 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 3.58 (s, 2H), 1.25 (t, J=7.2 Hz, 3H).

Workup

  1. customto afford a light yellow solution
  2. concentrationwas concentrated to 30 mL
  3. customThe concentrate was partitioned between ethyl acetate and half-saturated NaHCO3 solution
  4. extractionThe aqueous was extracted with ethyl acetate
  5. washThe organic was washed with water, brine
  6. customseparated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d51ee3a4f922467d87993102ca99925b
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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