Methyl iodide → 5-Hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2350991Notes

Reaction equation

HRID 2350991 reaction equation
C[I:2].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[OH:25][C:26]1[C:27]([CH3:41])=[C:28]([CH3:40])[C:29]2[O:33][CH:32]([CH2:34][CH2:35][CH2:36]O)[S:31][C:30]=2[C:38]=1[CH3:39]>CN(C)C=O>[OH:25][C:26]1[C:27]([CH3:41])=[C:28]([CH3:40])[C:29]2[O:33][CH:32]([CH2:34][CH2:35][CH2:36][I:2])[S:31][C:30]=2[C:38]=1[CH3:39]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 7540Triphenyl phosphiteHCID 1275772-(3-Hydroxypropyl)-4,6,7-trimethyl-2H-1,3-benzoxathiol-5-ol

Product 1

HCID 135920605-Hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 ml of methyl iodide were added to 0.67 g of triphenyl phosphite, and then the temperature of the reaction mixture was raised to reflux temperature, after which the reaction was continued for 1 hour at a bath temperature of 100° C. The temperature of the reaction mixture was reduced to room temperature, and then 0.5 g of 3-(5-hydroxy-4,6,7-trimethyl-1,3,-benzoxathiole-2-yl)propanol (prepared as described in Example 71), 1 ml of methyl iodide and 0.5 ml of dimethylformamide were added to the reaction mixture. The reaction was continued for 3 days at room temperature. At the end of this time, the title compound, having the same properties as the product of (a) above, was obtained by the same treatment and separation procedures as in (a).

Workup

  1. temperaturethe temperature of the reaction mixture was raised
  2. temperatureto reflux temperature
  3. customtemperature of 100° C
  4. customwas reduced to room temperature
  5. waitThe reaction was continued for 3 days at room temperature

Sources & evidence

ORD record
ord-a307ac078fc640cb85e7f0d9acc34647
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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