Hydrochloric Acid → (S)-3-(1-methoxypropan-2-yloxy)-5-(4-(methylsulfonyl)phenoxy)benzoic acid

HRID 644087Notes

Reaction equation

HRID 644087 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:25])[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:13]=1)[C:9]#N.[OH2:26].[OH-:27].[Na+].Cl>C(O)C.CC(OC)(C)C>[CH3:1][O:2][CH2:3][C@H:4]([CH3:25])[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:13]=1)[C:9]([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59263302HCID 59263302, compound

Product 1

HCID 59263311(S)-3-(1-methoxypropan-2-yloxy)-5-(4-(methylsulfonyl)phenoxy)benzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzonitrile (0.1 g, 0.27 mmol) was dissolved in ethanol (1.0 ml) and charged to a 5 ml round bottomed flask equipped with condenser and magnetic stirrer. Water (0.2 ml, 11.1 mmol) was added, followed by sodium hydroxide (18.9M in water, 0.2 ml, 3.78 mmol). The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled to ambient temperature, and the solvent was evaporated in vacuo. The residue was partitioned between water (10 ml) and MTBE (10 ml) and the layers were separated. The aqueous phase was acidified to pH1 with 2M HCl (2.5 ml, 5 mmol) and MTBE (10 ml) was added to extract the product. The MTBE extract was dried over MgSO4, and then evaporated in vacuo to afford a pale yellow oil (0.1 g, 100% yield).

Workup

  1. additioncharged to a 5 ml round bottomed flask
  2. customequipped with condenser and magnetic stirrer
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 18 hours
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was partitioned between water (10 ml) and MTBE (10 ml)
  7. customthe layers were separated
  8. additionwas added
  9. extractionto extract the product
  10. extractionThe MTBE extract
  11. dry with materialwas dried over MgSO4
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-7888ffb3cd1e470a89948ffc27a7f95a
Source dataset
uspto-grants-2010_04
Patent number
US07700640B2

Reaction notes

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