Methanol → HCID 19782774, compound

HRID 1461891Notes

Reaction equation

HRID 1461891 reaction equation
[C:1]([SH:5])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO.Br[CH:11]([CH2:14][CH2:15]Cl)[CH:12]=[O:13]>O>[CH:12]([C:11]1([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:15][CH2:14]1)=[O:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 6387tert-Butyl mercaptanHCID 14798Sodium HydroxideHCID 19782772HCID 19782772, compound

Product 1

HCID 19782774HCID 19782774, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an atmosphere of nitrogen and while cooling with ice, 112 ml of tert-butyl mercaptan are added dropwise over 10 minutes to a solution, cooled to 5° C., of 80 g of sodium hydroxide in 750 ml of water. Then 50 ml of methanol are added. After 1 hour, 151 g of 2-bromo-4-chlorobutanal (89.5%) are added dropwise over 15 minutes with efficient stirring and cooling, whereupon the temperature of the reaction mixture rises from 5° to 20° C. After 30 minutes, the mixture is extracted 4 times with diethyl ether. The combined organic phases are washed twice with a saturated solution of sodium chloride and dried over magnesium sulfate. The residue obtained after concentrating the residue on a rotary evaporator is fractionated over a 30 cm packed column, affording 89 g of 1-formyl-1-tert-butylthiocyclopropane in 89% purity. Boiling point: 112°-114° C./8 400 Pa.

Workup

  1. additionare added dropwise over 10 minutes to a solution
  2. temperaturecooling, whereupon the temperature of the reaction mixture
  3. customrises from 5° to 20° C
  4. waitAfter 30 minutes
  5. extractionthe mixture is extracted 4 times with diethyl ether
  6. washThe combined organic phases are washed twice with a saturated solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe residue obtained
  9. concentrationafter concentrating the residue
  10. customon a rotary evaporator

Sources & evidence

ORD record
ord-e3427e4cfb7740fe8d5f4844bf0da4e6
Source dataset
uspto-grants-1991_12
Patent number
US05077439

Reaction notes

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