Ethanol hydrochloride → Ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate

HRID 1183666Notes

Reaction equation

HRID 1183666 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH2:15][C:16]([OH:18])=[O:17])[CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[CH2:3][CH2:2]1.[CH2:19](O)[CH3:20].Cl>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 579955402-(3-(Cyclopropylmethoxy)-4-nitrophenyl)acetic acid

Product 1

HCID 57995474Ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate

Procedure

2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetic acid (40 g, 143 mmol) was dissolved in 20% EtOH—HCl solution (200 ml) and refluxed for 3 h to convert the starting material to ester. The volatiles were removed under reduced pressure and the residue was extracted with ethyl acetate (×2). The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by re crystallization to ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate (38 g) as pale yellow solid.

Workup

  1. temperaturerefluxed for 3 h
  2. customThe volatiles were removed under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate (×2)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by re crystallization to ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate (38 g) as pale yellow solid

Sources & evidence

ORD record
ord-8f10c755f1f94d5abe82e713977c7008
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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