Sodium Hydroxide → HCID 18790105, compound

HRID 1107162Notes

Reaction equation

HRID 1107162 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:13]([CH:16]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]([CH3:23])([CH3:22])[C:18]([O:20]C)=[O:19])(=[O:15])=[O:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]>O.CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:13]([CH:16]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:17]([CH3:22])([CH3:23])[C:18]([OH:20])=[O:19])(=[O:14])=[O:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18790127Methyl 3-(3,4-dimethoxybenzenesulfonyl)-2,2-dimethyl-7-phenylheptanoate

Product 1

HCID 18790105HCID 18790105, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.31 g, 7.7 mmol) in water (4 mL) is added to a solution of methyl 3-(3,4-dimethoxybenzenesulfonyl)-2,2-dimethyl-7-phenylheptanoate (0.78 g, 1.7 mmol) in MeOH (6 mL). The reaction is heated at reflux 24 hours. The solvent is then removed in vacuo, CH2Cl2 (20 mL) added and the solution washed with 1 N HCl (2×40 mL). The organic layer is dried over MgSO4 and the solvent removed in vacuo to afford 3-(3,4-dimethoxyphenylsulfonyl)-2,2-dimethyl-7-phenylheptanoic acid (0.54 g, 73%) 1H NMR (300 MHz, CDCl3) δ 7.47 (dd, J=8.5, 2.1 Hz, 1H), 7.36 (d, J=2.1 Hz, 1H), 7.26-7.16 (m, 3H), 7.02 (d, J=7.0 Hz, 2H), 6.90 (d, J=8.4 Hz, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 3.76-3.73 (m, 1H), 2.46-2.41 (m, 2H), 2.06-2.00 (m, 1H), 1.65-1.60 (m, 2H), 1.48 (s, 3H), 1.45-1.35 (m, 3H), 1.29 (s, 3H); MS (FAB) m/e 434 (M+).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux 24 hours
  3. customThe solvent is then removed in vacuo, CH2Cl2 (20 mL)
  4. additionadded
  5. washthe solution washed with 1 N HCl (2×40 mL)
  6. dry with materialThe organic layer is dried over MgSO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-03ad8db4215c434294ebb0a6f63ad4e7
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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