HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Methanol → 3-Methyl-4'-nitrobiphenyl-4-carboxylic acid

HRID 2356826
Notes
Print preview

Reaction equation

HRID 2356826 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].CO.O.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 59385226Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

Product 1

HCID 593852883-Methyl-4'-nitrobiphenyl-4-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

Methyl 3-methyl-4′-nitrobiphenyl-4-carboxylate (0.70 g, 2.1 mmol) was suspended in THF (5 mL), MeOH (5 mL) and water (2.5 mL), and NaOH (0.41 g, 10.3 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated in vacuo and purified by reversed-phase HPLC to give 0.498 g (94%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 7.62-7.68 (m, 2H), 7.91-8.05 (m 3H), 7.18 (t, 1H), 8.31 (d, 1H).

Workup

  1. temperatureUpon cooling to rt
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-77483ebdeec74dcaa8a287ad1ee30b8c
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759376B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes