Ethanol hydrochloride → Ethyl 2-(4-fluoro-3-methylphenyl)acetate

HRID 546775Notes

Reaction equation

HRID 546775 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](N)=[O:10])=[CH:4][C:3]=1[CH3:12].Cl.[CH2:14]([OH:16])[CH3:15]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:16][CH2:14][CH3:15])=[O:10])=[CH:4][C:3]=1[CH3:12]

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 668394032-(4-Fluoro-3-methylphenyl)acetamide

Product 1

HCID 53419406Ethyl 2-(4-fluoro-3-methylphenyl)acetate

Conditions

Temperature
85 °C

Procedure

2-(4-Fluoro-3-methylphenyl)acetamide (863 mg) was dissolved in saturated hydrochloric acid/ethanol (20 ml), and the reaction solution was stirred at 85° C. for 10 hours. The reaction solution was concentrated under reduced pressure and then diluted with ethyl acetate, followed by separation with water. The organic layer was washed with saturated aqueous sodium bicarbonate and brine and then dried over magnesium sulfate. 919 mg of the title compound was obtained by concentration under reduced pressure. The property values of the compound are as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. customfollowed by separation with water
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-fe4bdb41fc8048189acf8eb1a3c10bc9
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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