Iodine → 2-Hydroxymethyl-3-methyl-5-iodothiophene

HRID 460973Notes

Reaction equation

HRID 460973 reaction equation
[I:1]I.[OH:3][CH2:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH3:10]>C1C=CC=CC=1>[OH:3][CH2:4][C:5]1[S:6][C:7]([I:1])=[CH:8][C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 807IodineHCID 12875263(3-Methylthiophen-2-yl)methanol

Product 1

HCID 191047842-Hydroxymethyl-3-methyl-5-iodothiophene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.58 G. (33 mmol) of mercuric oxide and 7.62 g. (30 mmol) of iodine were added alternately in small amounts to a vigorously sitrred solution of 3.84 g. (30 mmol) of 2-hydroxymethyl-3-methylthiophene in 30 ml. of benzene. The reaction was kept at room temperature by cooling with an ice bath. The orange mercuric iodide which precipitated was filtered and washed well with benzene. The combined organic solutions were washed with sodium thiosulfate and saturated sodium chloride solution, dried and evaporated to yield crude 2-hydroxymethyl-3-methyl-5-iodothiophene as a colorless oil.

Workup

  1. customwas kept at room temperature
  2. temperatureby cooling with an ice bath
  3. customThe orange mercuric iodide which precipitated
  4. filtrationwas filtered
  5. washwashed well with benzene
  6. washThe combined organic solutions were washed with sodium thiosulfate and saturated sodium chloride solution
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-64d5752f6ff2429cbe272b3e5f9dc8e6
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Reaction notes

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