Sodium peroxyborate tetrahydrate → Ethyl 5-phenyl-2-sulfo-1-cyclohexene-1-carboxylate

HRID 2299213Notes

Reaction equation

HRID 2299213 reaction equation
[OH2:1].[OH2:2].[OH2:3].O.B(O[O-])([O-])[O-].[Na+].[Na+].[Na+].[SH:13][C:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][C:15]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(O)(=O)C>[C:20]1([CH:17]2[CH2:16][C:15]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:14]([S:13]([OH:3])(=[O:2])=[O:1])[CH2:19][CH2:18]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 18380057Sodium peroxyborate tetrahydrateHCID 21958083Ethyl 2-mercapto-5-phenyl-1-cyclohexene-1-carboxylate

Product 1

HCID 18380061Ethyl 5-phenyl-2-sulfo-1-cyclohexene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
52.5 °C

Procedure

Sodium peroxyborate tetrahydrate (35.2 g) was admixed with acetic acid (200 ml) and heated to 50 to 55° C. and then a solution of ethyl 2-mercapto-5-phenyl-1-cyclohexene-1-carboxylate synthesized in Reference Example 13 (20 g) in acetic acid (200 ml) was added dropwise over 2 hours. The mixture was stirred at 50 to 55° C. for 3 hours and then at 80 to 85° C. for 5 hours and concentrated under reduced pressure. The residue was combined with acetonitrile (500 ml) and stirred at room temperature for 1 hour and the resultant insolubles were filtered off. The insolubles were washed with acetonitrile (20 ml) and the filtrate and the washing were combined and concentrated under reduced pressure, and the resultant residue was dissolved in a mixture of acetonitrile (500 ml) and methanol (500 ml) and stirred at room temperature for 2 hours. The resultant insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was combined with diisopropyl ether (500 ml) and the pellet which precipitated was isolated by a filtration to obtain ethyl 5-phenyl-2-sulfo-1-cyclohexene-1-carboxylate as a white powder (40.4 g) containing inorganic substances.

Workup

  1. additionwas added dropwise over 2 hours
  2. waitat 80 to 85° C. for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. stirringstirred at room temperature for 1 hour
  5. filtrationthe resultant insolubles were filtered off
  6. washThe insolubles were washed with acetonitrile (20 ml)
  7. concentrationconcentrated under reduced pressure
  8. dissolutionthe resultant residue was dissolved in a mixture of acetonitrile (500 ml) and methanol (500 ml)
  9. stirringstirred at room temperature for 2 hours
  10. filtrationThe resultant insolubles were filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customthe pellet which precipitated
  13. customwas isolated by a filtration

Sources & evidence

ORD record
ord-aa77260b07ea4981a03cb84bdce4933f
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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