Iodine → 1,2-Dithiolane

HRID 1881344Notes

Reaction equation

HRID 1881344 reaction equation
S[CH:2]([SH:21])[C:3]([CH:5]([OH:20])[C:6]([CH2:18][OH:19])([CH2:16][OH:17])[C:7](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:8])=O.[OH-].[Na+].II.[O-][S:27]([O-])(=S)=O.[Na+].[Na+]>CCO.C(Cl)Cl>[S:21]1[CH2:2][CH2:3][CH2:5][S:27]1.[CH:9](=[C:7]([C:6]([CH2:5][OH:20])([CH2:16][OH:17])[CH2:18][OH:19])[OH:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 131730077Dimercaptoacetyl monobenzalpentaerythritol

Product 2

HCID 790451,2-DithiolaneHCID 534451662,2-Bis(hydroxymethyl)-4-phenylbut-3-ene-1,3-diol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimercaptoacetyl monobenzalpentaerythritol (4.1 mmol) in EtOH (20 ml) is treated with 10 ml of aqueous 1 N NaOH at room temperature for 1 h. The mixture is diluted with CH2Cl2 (100 ml) and then an aqueous solution of 0.1 M iodine (4.5 mmol) is added dropwise. The reaction mixture was stirred for 2 hours at room temperature and 1 mmol of Na2S2O3 (1 M aqueous solution) was added to the reaction mixture. The organic phase was separated, washed with water (3(200 mL), dried with magnesium sulfate, and evaporated at room temperature. The crude product is chromatographed on silica gel (200 mL) using a solvent mixture of hexane and ethyl acetate (40:20) as eluent to give 1,2-dithiolane of monobenzalpentaerythritol. Step 5: Synthesis of 1,2-dithiolane pentaerythritol

Workup

  1. customThe organic phase was separated
  2. washwashed with water (3(200 mL)
  3. dry with materialdried with magnesium sulfate
  4. customevaporated at room temperature
  5. customThe crude product is chromatographed on silica gel (200 mL)
  6. additiona solvent mixture of hexane and ethyl acetate (40:20) as eluent

Sources & evidence

ORD record
ord-94a34d52e5394d52a26b7a6e2cf10203
Source dataset
uspto-grants-2012_11
Patent number
US08318795B2

Reaction notes

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