Hydrochloric Acid → HCID 86662326, compound

HRID 2367903Notes

Reaction equation

HRID 2367903 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]1[S:16](=O)[CH2:15][CH2:14][CH2:13]1.Cl.[F:19][C:20]([F:43])([S:39]([O-:42])(=[O:41])=[O:40])[CH:21]([O:26][C:27]([C:29]12[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2)=[O:28])[C:22]([F:25])([F:24])[F:23].[Na+]>CO>[C:29]12([C:27]([O:26][CH:21]([C:22]([F:25])([F:23])[F:24])[C:20]([F:19])([F:43])[S:39]([O-:42])(=[O:40])=[O:41])=[O:28])[CH2:30][CH:31]3[CH2:37][CH:35]([CH2:34][CH:33]([CH2:32]3)[CH2:38]1)[CH2:36]2.[OH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([S+:16]2[CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1128Tetramethylene sulfoxideHCID 70051-NaphtholHCID 86662327Sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate

Product 1

HCID 86662326HCID 86662326, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-16 °C

Procedure

First 10 g (0.069 mol) of 1-naphthol and 7.2 g (0.069 mol) of tetramethylene sulfoxide were dissolved in 50 g of methanol and cooled at −16° C. An excess amount of hydrogen chloride gas was fed into the solution at a temperature below 20° C. Nitrogen was bubbled into the solution to expel the excess of hydrogen chloride gas whereupon the reaction solution was concentrated. Water and diisopropyl ether were added to the concentrate, from which a water layer, aqueous solution of 4-hydroxynaphthyl-1-tetrahydrothiophenium chloride was separated. Next, the aqueous solution (corresponding to 0.023 mol) of 4-hydroxynaphthyl-1-tetrahydrothlophenium chloride was mixed with an aqueous solution (corresponding to 0.021 mol) of sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate which was synthesized according to the formulation described in JP-A 2007-145797 (or U.S. Pat. No. 7,511,169). The mixture was extracted with 100 g of dichloromethane and 50 g of methyl isobutyl ketone. The organic layer was washed with water, the solvents were distilled off in vacuum, and isopropyl ether was added to the residue for crystallization. Subsequent filtration and drying gave the target compound. White crystal, 6.2 g, yield 43%.

Workup

  1. customwas fed into the solution at a temperature below 20° C
  2. customNitrogen was bubbled into the solution
  3. concentrationwas concentrated
  4. additionWater and diisopropyl ether were added to the concentrate, from which a water layer, aqueous solution of 4-hydroxynaphthyl-1-tetrahydrothiophenium chloride
  5. customwas separated
  6. customwas synthesized
  7. extractionThe mixture was extracted with 100 g of dichloromethane and 50 g of methyl isobutyl ketone
  8. washThe organic layer was washed with water
  9. distillationthe solvents were distilled off in vacuum, and isopropyl ether
  10. additionwas added to the residue for crystallization
  11. filtrationSubsequent filtration
  12. customdrying
  13. customgave the target compound

Sources & evidence

ORD record
ord-d8362b8a51ba4a48bc19f7e8ba5e84c3
Source dataset
uspto-grants-2014_04
Patent number
US08703384B2

Reaction notes

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