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

HRID 841883Notes

Reaction equation

HRID 841883 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-6fbdb866090948ff8f8981f37e8e7be3
Source dataset
uspto-grants-2002_04
Patent number
US06372733B1

Reaction notes

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