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

HRID 2299200Notes

Reaction equation

HRID 2299200 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][CH2:17][CH2:16][C:15]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)(=O)C>[S:13]([C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])([OH:3])(=[O:2])=[O:1]

Participants

4

Reactant 2

HCID 18380057Sodium peroxyborate tetrahydrateHCID 18380060Ethyl 2-sulfanylcyclohex-1-ene-1-carboxylate

Product 1

HCID 6917303Ethyl 2-sulfo-1-cyclohexene-1-carboxylateYield 166.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
52.5 °C

Procedure

Sodium peroxyborate tetrahydrate (22.3 g) was admixed with acetic acid (120 ml) and heated to 50 to 55° C. and then a solution of ethyl 2-mercapto-1-cyclohexene-1-carboxylate (9.0 g) in acetic acid (15 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 (200 ml) and stirred at room temperature for 3 hours and the resultant insolubles were filtered off. The insolubles were washed with acetonitrile (50 ml) and the filtrate and the washing were combined and concentrated under reduced pressure, and the resultant residue was dissolved in acetonitrile (150 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 (300 ml) and the powder which precipitated was isolated by filtration to obtain ethyl 2-sulfo-1-cyclohexene-1-carboxylate as a white powder (18.8 g) containing inorganic substances.

Workup

  1. waitat 80 to 85° C. for 5 hours
  2. concentrationconcentrated under reduced pressure
  3. stirringstirred at room temperature for 3 hours
  4. filtrationthe resultant insolubles were filtered off
  5. washThe insolubles were washed with acetonitrile (50 ml)
  6. concentrationconcentrated under reduced pressure
  7. dissolutionthe resultant residue was dissolved in acetonitrile (150 ml)
  8. stirringstirred at room temperature for 2 hours
  9. filtrationThe resultant insolubles were filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe powder which precipitated
  12. customwas isolated by filtration

Sources & evidence

ORD record
ord-5dcd4db7339c468291c00f34808f050a
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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