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

HRID 1183733Notes

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

Conditions

Temperature: 0 °C

Procedure

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, the residue dissolved in H2O, acidified with 6N HCl to pH-2. The solid material was collected via filtration, washed with water, dried under reduced pressure to yield 6.5 g (90%) of 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetic acid as a yellow solid.

Workup

temperatureThe reaction mixture was heated gently up to 60° C. for 5 h
customAfter complete conversion of starting material solvent was evaporated under reduced pressure
dissolutionthe residue dissolved in H2O
filtrationThe solid material was collected via filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-5328a5929d154d3d8c0acf00b66defa7
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664249B2

Reaction notes

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