Hydrochloric Acid → HCID 19855336, compound

HRID 1758171Notes

Reaction equation

HRID 1758171 reaction equation
[C:1]1([S:7](OC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[K+].[CH3:13][C@H:14]1[C@H:19]([CH2:20][CH:21]=[CH2:22])[CH2:18][CH2:17][C:16](=[O:23])[CH2:15]1.Cl>C(COC)OC>[CH3:13][CH:14]1[CH2:15][C:16](=[O:23])[CH:17]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:18][CH:19]1[CH2:20][CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 82127Potassium hydrideHCID 2759784Methyl benzenesulfinateHCID 15670663(3R,4S)-3-Methyl-4-(prop-2-en-1-yl)cyclohexan-1-one

Product 1

HCID 19855336HCID 19855336, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. mixture of 16.9 g. (0.109 mole) of methyl benzenesulfinate and 8.68 g. (0.217 mole) of potassium hydride in 100 ml. of dimethoxyethane was slowly added a solution of 15.0 g. (0.0987 mole) of trans-3-methyl-4-(2-propenyl)cyclohexanone in 50 ml. of dimethoxyethane. The reaction was stirred 30 minutes longer at 0° C. and then cautiously added to 500 ml. of ice-saturated sodium chloride and 45 ml. 6 N hydrochloric acid. The quenched reaction mixture was extracted once with 300 ml. ether and once with 200 ml. dichloromethane. The organic extract was dried over magnesium sulfate and evaporated to give a quantitative yield of the title compound as a semisolid mixture of axial and equatorial sulfenates. Crystallization from ether yields 7.8 g. of pure axial sulfenate.

Workup

  1. additionTo a 0° C. mixture of 16.9 g
  2. additioncautiously added to 500 ml
  3. customThe quenched reaction mixture
  4. extractionwas extracted once with 300 ml
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. customevaporated
  8. customto give

Sources & evidence

ORD record
ord-9c5a3a58006347efb9331fe6dcf49c24
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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