Hydrochloric Acid → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

HRID 1673165Notes

Reaction equation

HRID 1673165 reaction equation
C([O:9][CH2:10][CH:11]1[CH2:16][O:15][C:14]2=[CH:17][S:18][CH:19]=[C:13]2[O:12]1)(=O)C1C=CC=CC=1.[OH-].[K+].Cl>C(O)C.O>[O:15]1[CH2:16][CH:11]([CH2:10][OH:9])[O:12][C:13]2=[CH:19][S:18][CH:17]=[C:14]12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66919222HCID 66919222, compound

Product 1

HCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanolYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 100 mL round bottom flask, 7.5 g (0.027 mol) (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methyl benzoate was dissolved in a minimal amount of warm ethanol and dropwise added to a refluxing solution of 4.58 g (0.081 mol) potassium hydroxide in 50 mL water. After heating overnight, the reaction was cooled to room temperature and acidified to pH 7 by dropwise addition of concentrated hydrochloric acid. The reaction mixture was extracted with methylene chloride. The organic fractions were combined and the solvent removed under reduced pressure. Purification by column chromatography provided 3.95 g (85% yield) of (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methanol. Structure was confirmed by 1H/13C NMR and LC-MS.

Workup

  1. temperatureAfter heating overnight
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. customthe solvent removed under reduced pressure
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-e2c1ae3aead747b39200ac84af366b2e
Source dataset
uspto-grants-2011_08
Patent number
US07999121B2

Reaction notes

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