Iodine → [Disulfanediyldi(2,1-phenylene)]dimethanol

HRID 1742800Notes

Reaction equation

HRID 1742800 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-:17].[Na+].II.[Na+].[Cl-]>O1CCOCC1.CO.O.O1CCCC1>[OH:17][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[S:1][S:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

10

Reactant 5

HCID 807IodineHCID 5234Sodium ChlorideHCID 54432-Mercaptobenzoic AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 816729[Disulfanediyldi(2,1-phenylene)]dimethanol

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 30.8 g (0.20 mol) of o-mercaptobenzoic acid in 300 ml of dioxane was added to a mixture of 15.2 g (0.40 mol) lithium aluminum hydride in 300 ml of dioxane. 160 ml of tetrahydrofuran ("THF") was slowly added to this mixture with some loss of material due to bumping. The mixture was stirred for 2 hours followed by the slow addition of 15.2 ml of water, then 15.2 ml of 15% NaOH and finally 45.6 ml of water. The mixture was filtered with a methanol wash and the filtrate was concentrated to 20.0 g of oil. Methanol (250 ml) and 18.1 g (0.07 mol) of iodine were added and the mixture was stirred over the weekend. An equal volume of saturated NaCl solution was added and the solid was collected, washed with water, and recrystallized from aqueous ethanol. The yield of bis(2-hydroxymethylphenyl) disulfide was 10.0 g and had amp of 138.5°-139.5° C.

Workup

  1. filtrationThe mixture was filtered with a methanol
  2. washwash
  3. concentrationthe filtrate was concentrated to 20.0 g of oil
  4. stirringthe mixture was stirred over the weekend
  5. customthe solid was collected
  6. washwashed with water
  7. customrecrystallized from aqueous ethanol
  8. customamp of 138.5°-139.5° C.

Sources & evidence

ORD record
ord-3dde963fda8d4593920016b267a4ed67
Source dataset
uspto-grants-1994_08
Patent number
US05342724

Reaction notes

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