Benzene → 5-Acetoxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2308877Notes

Reaction equation

HRID 2308877 reaction equation
[OH:1][C:2]1[C:3]([CH3:20])=[C:4]([CH3:19])[C:5]2[O:9][CH:8]([CH2:10][CH2:11][CH2:12][O:13][CH2:14][O:15][CH3:16])[S:7][C:6]=2[C:17]=1[CH3:18].[C:21](OC(=O)C)(=[O:23])[CH3:22].C1C=CC=CC=1>N1C=CC=CC=1>[C:21]([O:1][C:2]1[C:3]([CH3:20])=[C:4]([CH3:19])[C:5]2[O:9][CH:8]([CH2:10][CH2:11][CH2:12][O:13][CH2:14][O:15][CH3:16])[S:7][C:6]=2[C:17]=1[CH3:18])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7918Acetic AnhydrideHCID 148021895-Hydroxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Product 1

HCID 148021905-Acetoxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mg of 5-hydroxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 83) were dissolved in 1 ml of pyridine, and 50 mg of acetic anhydride were added. The reaction mixture was allowed to react for 20 hours at room temperature. Benzene was then added to the reaction mixture, and the benzene solution was washed with water and then dried over anhydrous sodium sulfate. The benzene was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography. The title compound was obtained from the fraction eluted with a 20:1 by volume mixture of benzene and ethyl acetate.

Workup

  1. customto react for 20 hours at room temperature
  2. washthe benzene solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe benzene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d6ade16802ec4b11ab42ee4907a6d1e6
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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