Ethanol → Ethyl 2-(3-fluorophenyl)acetate

HRID 76966

Reaction equation

HRID 76966 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH2:17](O)[CH3:18]>>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 676173-Fluorophenylacetic acid

Product 1

HCID 11735538Ethyl 2-(3-fluorophenyl)acetateYield 85%

Procedure

To a solution of 3-fluorophenyl acetic acid (10.0 g, 64.9 mmol) in ethanol (300 mL), is added a catalytic amount of H2SO4 (98%, 1 mL) and the mixture reacted for 12 hours at 100° C. (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between EtOAc and water; the organic layer is separated and dried over Na2SO4 in order to obtain 10.1 g of (I8) as a white solid (85% yield).

Workup

  1. customthe mixture reacted for 12 hours at 100° C. (LC-MS monitoring: complete conversion)
  2. customThe solvent is evaporated
  3. customthe residue is partitioned between EtOAc and water
  4. customthe organic layer is separated
  5. dry with materialdried over Na2SO4 in order

Sources & evidence

ORD record
ord-38049ee9739249dfa2ee123b242c4d2b
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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