Sulfuric Acid → HCID 10654447, compound

HRID 1615153Notes

Reaction equation

HRID 1615153 reaction equation
[CH2:1]([C:4]1([OH:14])[CH2:13][CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5]1)[CH:2]=[CH2:3].S(=O)(=O)(O)O>O>[CH2:1]([C:4]1([OH:14])[CH2:13][CH2:12][CH2:11][C:6](=[O:7])[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10703113HCID 10703113, compound

Product 1

HCID 10654447HCID 10654447, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-allyl-1,4-dioxa-spiro[4.5]decan-7-ol (12.8 g) and 0.5 M sulfuric acid (13 mL) is stirred at room temperature for 1 h. Water is then added and the resulting mixture is extracted with diethyl ether. The combined extract is washed with water (3×), brine, and dried (MgSO4). The solvent is evaporated and the residue is triturated with diispropyl ether/heptane 1:1 to give the title compound. Yield: 2.7 g (27% of theory); TLC [silicagel, cyclohexane/ethyl acetate 1:1]: rf=0.55; Mass spectrum (ESI+): m/z=155 [M+H]+.

Workup

  1. extractionthe resulting mixture is extracted with diethyl ether
  2. extractionThe combined extract
  3. washis washed with water (3×), brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated
  6. customthe residue is triturated with diispropyl ether/heptane 1:1

Sources & evidence

ORD record
ord-57f2358750634b52b67ac607a10dba0b
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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