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

HRID 369542Notes

Reaction equation

HRID 369542 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]([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:13]([N+:26]([O-:28])=[O:27])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].CO.O.[OH-].[Li+].Cl>C1COCC1.[Cl-].[Na+].O.O>[CH3:25][C@H:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)=[CH:12][C:13]=1[N+:26]([O-:28])=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 54451763HCID 54451763, compound

Product 1

HCID 22864004(S)-4'-(1-Methylheptyloxy)-3'-(nitro)-4-biphenylcarboxylic acidYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ester 41a (1.679 g, 4.36 mmol) was dissolved in 10 ml of THF, and with vigorous stirring methanol (40 ml) was added, followed by water (approximately 10 ml) until the solution remained milky white. To this suspension was added lithium hydroxide monohydrate (1.83 g, 43.6 mmol). The reaction mixture was refluxed overnight and was then acidified with concentrated HCl. Brine was added, the reaction mixture was extracted with ether and the organic layer was washed with brine and dried over MgSO4. Evaporation of the solvent yielded 1.486 g (92%) of a light yellow solid.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed overnight
  3. extractionthe reaction mixture was extracted with ether
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4da0874fcb0544ef9e213e00a62ed9b7
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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