Hydrochloric Acid → HCID 12134604, compound

HRID 2308189Notes

Reaction equation

HRID 2308189 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][O:8][C:7]2[CH:10]=[CH:11][C:12]([C:14](C)=[O:15])=[CH:13][C:6]=2[O:5]1.[SH-].[Na+].Cl.[O-:20]Cl.[Na+]>>[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][O:8][C:7]2[CH:10]=[CH:11][C:12]([C:14]([OH:15])=[O:20])=[CH:13][C:6]=2[O:5]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 28015Sodium hydrosulfideHCID 154214401-[3-(Methoxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethan-1-oneHCID 23665760Sodium Hypochlorite

Product 1

HCID 12134604HCID 12134604, compound

Conditions

Temperature
65 °C

Procedure

To 13% (v/v) NaOCl (140 ml, purchased from Fluka) solution was added the titled compound of Example 2 (12.85 g, 0.0578 mol), followed by stirring. After being refluxed for 30 min while maintaining the temperature of 65° C., the reaction mixture was cooled down to a room temperature, stirred for 30 min and filtered to obtain a filtrate. To the said filtrate was added 10 ml of 25% (w/v) sodium hydrosulfide, and then, concentrated hydrochloric acid was added to adjust the pH by 3-4. The reaction mixture was filtered to give a solid, which was then washed and recrystallized with a mixture of water and ethanol (40:60, v/v) to prepare the titled compound (6.262 g, 48%, m.p. 119-123° C.).

Workup

  1. temperatureAfter being refluxed for 30 min
  2. temperaturethe reaction mixture was cooled down to a room temperature
  3. stirringstirred for 30 min
  4. filtrationfiltered
  5. customto obtain a filtrate
  6. filtrationThe reaction mixture was filtered
  7. customto give a solid, which
  8. washwas then washed
  9. customrecrystallized with a mixture of water and ethanol (40:60
  10. customv/v) to prepare the titled compound (6.262 g, 48%, m.p. 119-123° C.)

Sources & evidence

ORD record
ord-7993fbd2936f48109bc9fb7299f55d69
Source dataset
uspto-grants-2004_12
Patent number
US06835735B2

Reaction notes

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