Sodium Hydroxide → HCID 11554132, compound

HRID 550206Notes

Reaction equation

HRID 550206 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=3)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:11]=2)[CH:6]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[CH3:32][C:29]([CH3:30])([CH3:31])[C:28](=[O:33])[CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:15]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13]3)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:21][C:22]=1[CH3:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57871406HCID 57871406, compound

Product 1

HCID 11554132HCID 11554132, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Treat a solution of 6-{1-[4-(3,3-Dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-naphthalene-2-carboxylic acid methyl ester (0.53 g, 1.15 mmol) in THF (8 mL) and MeOH (16 mL) with 2N NaOH (2.9 mL, 5.8 mmol) and heat at 55° C. for 16 h. Concentrate the reaction mixture. Dilute the residue with in EtOAc (50 mL) and water (25 mL) and acidify the resulting mixture to pH 1 using 1N HCl. Discard the aqueous layer and wash the organic layer with brine, Dry the organic layer over Na2SO4, filter, and concentrate the filtrate to give the title compound as a yellow solid (0.45 g, 87%). MS (ES) m/e 447 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture
  2. additionDilute the residue with in EtOAc (50 mL) and water (25 mL)
  3. washwash the organic layer with brine
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-a82202a48ea549f3956955dac27c3557
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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