Water → Diprop-2-en-1-yl 3,3'-sulfanediyldipropanoate

HRID 1638138Notes

Reaction equation

HRID 1638138 reaction equation
[S:1]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:12](O)[CH:13]=[CH2:14].O.[C:17]1(C)[CH:22]=CC=C[CH:18]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[S:1]([CH2:7][CH2:8][C:9]([O:11][CH2:22][CH:17]=[CH2:18])=[O:10])[CH2:2][CH2:3][C:4]([O:6][CH2:12][CH:13]=[CH2:14])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7858Allyl AlcoholHCID 8096Thiodipropionic Acid

Product 1

HCID 14434560Diprop-2-en-1-yl 3,3'-sulfanediyldipropanoate

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 3,3'-thiodipropionic acid (17.82 g, 10 mmol), allyl alcohol (20.4 mL, 30 mmol) and p-toluenesulfonic acid (0.750 g) in 100 mL of toluene was refluxed for 8 h in a Dean-Stark apparatus to azeotropically remove water. The reaction mixture was quenched with saturated solution of sodium bicarbonate and the toluene layer was separated and washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and gave approximately 20 g of crude 3,3'-thiodipropionic acid, diallyl ester. This material was sufficiently pure by NMR and was used in the subsequent reaction.

Workup

  1. customThe reaction mixture was quenched with saturated solution of sodium bicarbonate
  2. customthe toluene layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a3b5e620ddb94bfcbe462170f3e1caae
Source dataset
uspto-grants-2000_03
Patent number
US06043358

Reaction notes

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