Hydrochloric Acid → HCID 59263315, compound

HRID 644086Notes

Reaction equation

HRID 644086 reaction equation
[CH3:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([O:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=2)[C:13]#N)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH2:26].[OH-:27].[Na+].Cl>C(O)C.CC(OC)(C)C>[CH3:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([O:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=2)[C:13]([OH:27])=[O:26])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 592633073-(4-Methanesulfonyl-phenoxy)-5-(2-methoxy-1-methyl-ethoxy)benzonitrile

Product 1

HCID 59263315HCID 59263315, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

3-(4-Methanesulfonyl-phenoxy)-5-(2-methoxy-1-methyl-ethoxy)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 a condenser. 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 room temperature, 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 pH 1 with 2M HCl (2.5 ml, 5 mmol) and MTBE (10 ml) was added to extract the product. This MTBE extract was dried over MgSO4, and then evaporated in vacuo to give the title product as a white solid (0.1 g, 100% yield).

Workup

  1. additioncharged to a 5 ml round bottomed flask
  2. customequipped with a condenser
  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. extractionThis MTBE extract
  11. dry with materialwas dried over MgSO4
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-05c806adcb1546189898b911f5a68aca
Source dataset
uspto-grants-2010_04
Patent number
US07700640B2

Reaction notes

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