Sodium Hydroxide → 2-(3-(Cyclopropylmethoxy)-4-nitrophenyl)acetic acid

HRID 1512453Notes

Reaction equation

HRID 1512453 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:15](C(OCC)=O)[C:16]([O:18]CC)=[O:17])[CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[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])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57995590Diethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)malonate

Product 1

HCID 579955402-(3-(Cyclopropylmethoxy)-4-nitrophenyl)acetic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound diethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)malonate (10 g) was dissolved in 100 mL ethanol and cooled to 0° C., NaOH solution (4 eq) was added slowly to the reaction mixture for about 15 min. The reaction mixture was heated gently up to 60° C. for 5 h. Progress of the reaction was monitored by TLC analysis. After complete conversion of starting material solvent was evaporated under reduced pressure, residue dissolved in H2O, acidified with 6N HCl to pH-2. Filtered the solid material washed with water, dried under reduced pressure to give 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetic acid (6.5 g) as a yellow solid. 1H-NMR (CDCl3, 200 MHz): 0.36 (m, 2H), 0.58 (m, 2H), 1.28 (m, 1H), 3.71 (s, 2H), 4.01 (d, 2H), 7.02 (d, 1H), 7.23 (s, 1H), 7.81 (d, 1H).

Workup

  1. temperatureThe reaction mixture was heated gently up to 60° C. for 5 h
  2. customAfter complete conversion of starting material solvent was evaporated under reduced pressure, residue
  3. dissolutiondissolved in H2O
  4. filtrationFiltered the solid material
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-96c0951225b04cc6a5b614a7c365b2cc
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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