Hydrochloric Acid → (S)-4'-(1-Methylnonyloxy)-3'-(nitro)-4-biphenylcarboxylic acid

HRID 369543Notes

Reaction equation

HRID 369543 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C@@H:18]([CH3:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:13]([N+:28]([O-:30])=[O:29])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].O.O.[OH-].[Li+].Cl>C1COCC1.CO>[CH3:27][C@H:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)=[CH:12][C:13]=1[N+:28]([O-:30])=[O:29])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 54059652(S)-Methyl-4'-(1-methylnonyloxy)-3'-(nitro)-4-biphenylcarboxylate

Product 1

HCID 54061531(S)-4'-(1-Methylnonyloxy)-3'-(nitro)-4-biphenylcarboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ester 41b (390 mg, 0.94 mmol) was dissolved in 3 ml THF and 15 ml methanol. Water was added with vigorous stirring until the solution remained cloudy, followed by the addition of lithium hydroxide monohydrate (56 mg, 1.30 mmol). After refluxing overnight, the solution was acidified with concentrated HCl and extracted with ether. The organic layer was washed with brine and dried over MgSO4. Evaporation of the solvent yielded 323 mg (86%) of a yellow solid.

Workup

  1. temperatureAfter refluxing overnight
  2. extractionextracted with ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-739b547755694095bede118415d471a8
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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