3-Hydroxybenzaldehyde → HCID 19885441, compound

HRID 846456Notes

Reaction equation

HRID 846456 reaction equation
[OH:1][C:2]1C=C(C=C[CH:9]=1)C=O.[SH:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]([OH:25])=O.Cl[CH2:27]Cl>[I-].[Zn+2].[I-]>[OH:25][C:23]1[CH:27]=[C:20]([CH:21]([S:17][C:2](=[O:1])[CH3:9])[S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:19]=[CH:18][CH:22]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6344Dichloromethane2×HCID 159702-Thiopheneacetic acidHCID 18050Methyl 3-mercaptopropionate

Product 1

HCID 19885441HCID 19885441, compound

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

To a dichloromethane (100 cc) solution of 3-hydroxybenzaldehyde (3.05 g, 25 mm) was added methyl 3-mercaptopropionate (3.0 g, 25 mm), thiolacetic acid (1.9 g, 25 mm), and dry zinc iodide (4.8 g, 15 mm). The mixture was reacted at room temPerature for 16 hrs and then diluted with dichloromethane, washed successively with 1N HCl, brine and dried with sodium sulphate. Removal of the solvent left a residue which was purified by chromatography (SiO2) to yield the title compound.

Workup

  1. customThe mixture was reacted at room temPerature for 16 hrs
  2. washwashed successively with 1N HCl, brine
  3. dry with materialdried with sodium sulphate
  4. customRemoval of the solvent
  5. waitleft a residue which
  6. customwas purified by chromatography (SiO2)

Sources & evidence

ORD record
ord-faa6f69580e84ce5b29551f25ba1c3e1
Source dataset
uspto-grants-1992_08
Patent number
US05136034

Reaction notes

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