Ethanol → ethyl 2-(2-formylphenoxy)acetate

HRID 619151Notes

Reaction equation

HRID 619151 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][C:7]([OH:9])=[O:8])=[O:2].[CH2:14](O)[CH3:15].OS(O)(=O)=O.C1(C)C=CC=CC=1>O>[CH2:14]([O:8][C:7]([CH2:6][O:5][C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[CH:1]=[O:2])=[O:9])[CH3:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 46533Acetic acid, (2-formylphenoxy)-

Product 1

HCID 345961ethyl 2-(2-formylphenoxy)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-formylphenoxyacetic acid (9.01 g, 0.05 mol), ethanol (4.6 g), concentrated H2SO4 (0.4 ml) and toluene (40 ml) was heated to reflux with azeotropic removal of water for 1 hour. The reaction mixture was poured into 10% KHCO3 (100 ml), the layers were separated and the aqueous layer was extracted with ether (2×75 ml). The organic layers were combined, and concentrated in vacuo to afford 9.1 g (95%) of 2-(ethoxycarbonylmethoxy)benzaldehyde.

Workup

  1. temperaturewas heated
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with ether (2×75 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c53395e0bc9347099604d4dff921057c
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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