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

HRID 2351005Notes

Reaction equation

HRID 2351005 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 was 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 then 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. customcondensed
  3. customby evaporation under reduced pressure
  4. additionthe condensate was poured into ice-water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe ethyl acetate was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-df3bd9eb2c45445c9ea95d5853cc143d
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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