Ethanol → Ethyl 3-methoxy-5-methylbenzeneacetate

HRID 1383356Notes

Reaction equation

HRID 1383356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[C:7]([CH3:9])[CH:8]=1.OS(O)(=O)=O.[CH3:19][CH2:20]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 39879Acetic acid, 5-methoxy-m-tolyl-

Product 1

HCID 22600115Ethyl 3-methoxy-5-methylbenzeneacetateYield 85%

Procedure

To a solution 3-methoxy-5-methylphenylacetic acid of (8.1 g; 0.045 mol; from step (iii) above) in EtOH (100 mL) was added H2SO4 (conc.), and the solution was left to stand for 40 hours. The reaction mixture was concentrated, and the crude product was partitioned between water and ether. The organic layer was washed with NaHCO3/aq and water, dried (Na2SO4), and evaporated to yield 8.0 g (85%) of the sub-title compound as a brown oil.

Workup

  1. waitthe solution was left
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was partitioned between water and ether
  4. washThe organic layer was washed with NaHCO3/aq and water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-89a21fa3af634c839105420dc7d6f966
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

Loading…