Ethanol → Ethyl 3-chloro-5-methylphenylacetate

HRID 1383363Notes

Reaction equation

HRID 1383363 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:18][CH3:19])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 226000812-(3-Chloro-5-methylphenyl)acetic acid

Product 1

HCID 22600092Ethyl 3-chloro-5-methylphenylacetateYield 85%

Procedure

A solution of 3-chloro-5-methylphenylacetic acid (5.0 g; 27.09 mmol; from step (iii) above) and H2SO4 (conc.; 0.1 mL) in EtOH (25 mL) was refluxed overnight. The solution was concentrated, and the resultant mixture digerated in Na2CO3 solution (75 mL). After extraction with ether (2×75 mL) the combined organic phases were washed with brine, dried (Na2SO4), and evaporated to yield 4.92 g (85%) of the sub-title compound.

Workup

  1. concentrationThe solution was concentrated
  2. extractionAfter extraction with ether (2×75 mL) the combined organic phases
  3. washwere washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-23bef4467ffa4b6186aa0b48109bfe36
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

Loading…