Ethanol → HCID 22118465, compound

HRID 1275465Notes

Reaction equation

HRID 1275465 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([OH:16])=[O:15])[C:9]=2[CH3:13])[S:4](=[O:18])(=[O:17])[CH2:3]1.S(=O)(=O)(O)O.[CH2:25](O)[CH3:26]>>[CH3:1][C:2]1([CH3:19])[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([O:16][CH2:25][CH3:26])=[O:15])[C:9]=2[CH3:13])[S:4](=[O:18])(=[O:17])[CH2:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 22118449HCID 22118449, compound

Product 1

HCID 22118465HCID 22118465, compoundYield 51%

Procedure

7.4 Grams (26 mmol) of 3,3,5-trimethyl-4-hydroxy-6-carboxythiochroman-1,1-dioxide was dissolved in 70 ml of ethanol, and 1 ml of sulfuric acid was added. The mixture was refluxed for 18 hours. The reaction mixture was concentrated, and the residue was dissolved in 300 ml of ethyl acetate and washed with 50 ml of water, with 200 ml of a 2 wt % sodium hydroxide aqueous solution and with 50 ml of water in this order. An organic layer was dried over sodium sulfate, and the solvent was distilled off. The resultant brown oil was purified by column chromatography (silica gel/ethyl acetate+hexane=1:1) to give 4.1 g (yield 51%) of a brownish oil.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in 300 ml of ethyl acetate
  4. washwashed with 50 ml of water, with 200 ml of a 2 wt % sodium hydroxide aqueous solution and with 50 ml of water in this order
  5. dry with materialAn organic layer was dried over sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resultant brown oil was purified by column chromatography (silica gel/ethyl acetate+hexane=1:1)

Sources & evidence

ORD record
ord-a5c1ca50e02f43bc90edb802da321179
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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