Sulfuric Acid → HCID 89488093, compound

HRID 630572

Reaction equation

HRID 630572 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH2:7]([OH:13])[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH3:12].OS(O)(=O)=O>N1C=CC=CC=1>[CH2:7]([O:13][C:1](=[O:5])[C:2]([O:13][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH3:12])=[O:3])[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 65578Oxalyl chlorideHCID 52811673-Hexenol

Product 1

HCID 89488093HCID 89488093, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Oxalyl chloride (12.7 g, 100.0 mmol) was added dropwise during 20 min to a stirred solution of (Z)-3-hexenol (20.0 g, 200.0 mmol) in pyridine (240 mL) at 0° C. The reaction mixture was allowed to warm up to room temperature during the week-end, then added to H2SO4 (50%, containing ice, 400 mL), extracted with ether (400 mL and 200 mL), treated again with H2SO4 (50%, containing ice, 400 mL), washed with a saturated solution of NaCl (200 mL) and a saturated solution of NaHCO3 (200 mL, 2×). The organic layer was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/diethyl ether 9:1) gave, after drying under vacuum (0.5 mbar, 1 h), 20.9 g (82%) of an oil.

Workup

  1. extractionextracted with ether (400 mL and 200 mL)
  2. additiontreated again with H2SO4 (50%, containing ice, 400 mL)
  3. washwashed with a saturated solution of NaCl (200 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customColumn chromatography (SiO2, heptane/diethyl ether 9:1) gave
  7. dry with materialafter drying under vacuum (0.5 mbar, 1 h), 20.9 g (82%) of an oil

Sources & evidence

ORD record
ord-2f9529cac7f0453cacc5882df03706ea
Source dataset
uspto-grants-2016_04
Patent number
US09315763B2

Linked notes

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