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

HRID 1512454Notes

Reaction equation

HRID 1512454 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 recrystallization 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 recrystallization to ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate (38 g) as pale yellow solid

Sources & evidence

ORD record
ord-242583184bf24da28e820b071661a1cb
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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