Water → HCID 14365385, compound

HRID 1111528Notes

Reaction equation

HRID 1111528 reaction equation
[BH4-].[Na+].[CH2:3]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1)=O)[C:4]([CH3:7])([CH3:6])[CH3:5].O.S(=O)(=O)(O)O>COCCOCCOC>[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([SH:16])=[CH:14][CH:15]=1)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 14365372HCID 14365372, compound

Product 1

HCID 14365385HCID 14365385, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

7.5 g (0.2 mol) of sodium borohydride in 140 ml of diethylene glycol dimethyl ether are initially introduced, and a solution of 41.6 g (0.2 mol) of 4-(neopentylcarbonyl)-thiophenol in 60 ml of diethylene glycol dimethyl ether are added at 30°-40° C. The mixture is further reacted at 120° C. for 2 hours, 100 ml of water are added with ice-cooling, the mixture is acidified with 20% strength sulphuric acid, and another 200 ml of water are added. The reaction mixture is now extracted with 250 ml of methylenechloride, the organic phase is extracted with 250 ml of water, dried over magnesium sulphate and distilled through a split ring column to give 23 g (60% of theory) of 4-(neohexyl)-thiophenol of boiling point 98° C./0.4 mbar.

Workup

  1. customThe mixture is further reacted at 120° C. for 2 hours
  2. temperaturecooling
  3. extractionThe reaction mixture is now extracted with 250 ml of methylenechloride
  4. extractionthe organic phase is extracted with 250 ml of water
  5. dry with materialdried over magnesium sulphate
  6. distillationdistilled through a split ring column

Sources & evidence

ORD record
ord-535a41c376fc4d93880fa55c64f2debe
Source dataset
uspto-grants-1990_12
Patent number
US04980510

Reaction notes

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