Sodium Hydroxide → HCID 18790103, compound

HRID 1107165Notes

Reaction equation

HRID 1107165 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:15]([CH3:21])([CH3:20])[C:16]([O:18]C)=[O:17])(=[O:13])=[O:12])=[CH:7][CH:6]=1>O.CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH:14]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:15]([CH3:21])([CH3:20])[C:16]([OH:18])=[O:17])(=[O:13])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18790130HCID 18790130, compound

Product 1

HCID 18790103HCID 18790103, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.40 g, 10 mmol) in water (6 mL) is added to a solution of methyl 3-(4-methoxybenzenesulfonyl)-2,2-dimethyl-7-phenylheptanoate (1.00 g, 2.4 mmol) in MeOH (8 mL). The reaction is heated at reflux 24 hours. The solvent is then removed in vacuo, CH2Cl2 (50 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 yield 3-(4-methoxybenzenesulfonyl)-2,2-dimethyl-7-phenylheptanoic acid (0.64 g, 66%): 1H NMR (300 MHz, CDCl3) δ 7.90-7.80 (m, 2H), 7.26-7.16 (m, 3H), 7.00-6.92 (m, 4H), 4.05-3.92 (m, 1H), 3.78 (s, 3H), 2.40-2.30 (m, 2H), 2.00-1.85 (m, 1H), 1.70-1.55 (m, 1H), 1.44 (s, 3H), 1.40-1.25 (m, 3H), 1.21 (s, 3H), 1.12-0.95 (m, 1H).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux 24 hours
  3. customThe solvent is then removed in vacuo, CH2Cl2 (50 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-5c0ce710138648bcb4824d0a568dc6ac
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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