Sulfuric Acid → 2-[3-(2-Dimethylaminoethoxy)propyl]-5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2308883Notes

Reaction equation

HRID 2308883 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH:9]1[S:13][C:12]2[C:14]([CH3:24])=[C:15]([O:20]COC)[C:16]([CH3:19])=[C:17]([CH3:18])[C:11]=2[O:10]1.S(=O)(=O)(O)O>C(O)(=O)C>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH:9]1[S:13][C:12]2[C:14]([CH3:24])=[C:15]([OH:20])[C:16]([CH3:19])=[C:17]([CH3:18])[C:11]=2[O:10]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 148021942-[3-(2-Dimethylaminoethoxy)propyl]-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

Product 1

HCID 148021952-[3-(2-Dimethylaminoethoxy)propyl]-5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

330 mg of 2-[3-(2-dimethylaminoethoxy)propyl]-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 88) were dissolved in 5 ml of acetic acid, and then 5 drops of 10% v/v aqueous sulfuric acid was added using a Komagome pipette; the mixture was then heated for 5 hours at 70°-75° C. The acetic acid solution and then condensed by evaporation under reduced pressure, and the condensate was poured into ice-water, neutralized with potassium carbonate and extracted with ethyl acetate. The ethyl acetate solution was washed with water and the dried over anhydrous sodium sulfate. The ethyl acetate was then distilled off under reduced pressure. The resulting residue was then subjected to silica gel column chromatography, and the title compound was obtained from the fraction eluted with a 20:1 by volume mixture of ethyl acetate and triethylamine.

Workup

  1. temperaturethe mixture was then heated for 5 hours at 70°-75° C
  2. customby evaporation under reduced pressure
  3. additionthe condensate was poured into ice-water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with water
  6. dry with materialthe dried over anhydrous sodium sulfate
  7. distillationThe ethyl acetate was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-310c7b8e52db40f0bcdb86191e9d159b
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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