Isopropanol → HCID 14326043, compound

HRID 1608022Notes

Reaction equation

HRID 1608022 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH3:10])([CH3:9])[CH2:4][C:5](=[O:8])[O:6]2.[CH:11]([OH:14])([CH3:13])[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH:11]([O:14][CH:7]1[O:6][C:5](=[O:8])[CH2:4][C:3]([CH3:10])([CH3:9])[CH:2]1[OH:1])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 545978HCID 545978, compound

Product 1

HCID 14326043HCID 14326043, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7 g of 5,6-epoxy-4,4-dimethyl-tetrahydro-pyr-2-one, 35 ml of isopropanol and 350 mg of p-toluene sulfonic acid was stirred at room temperature for 23 hours and was diluted with water. The mixture was extracted with methylene chloride and the combined extracts were washed with aqueous saturated sodium bicarbonate solution, was dried and evaporated to dryness under reduced pressure. The 9.18 g of residue was chromatographed over silica and was eluted with a 1-1 mixture of hexane-ethyl acetate to obtain 2.597 g of dl 6-isopropoxy-5-hydroxy-4,4-dimethyl-tetrahydro-pyr-2-one melting at 50° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. washthe combined extracts were washed with aqueous saturated sodium bicarbonate solution
  3. customwas dried
  4. customevaporated to dryness under reduced pressure
  5. customThe 9.18 g of residue was chromatographed over silica
  6. washwas eluted with a 1-1 mixture of hexane-ethyl acetate

Sources & evidence

ORD record
ord-f7ed4743f3ee4f7f93c242cd9ef4d4de
Source dataset
uspto-grants-1989_09
Patent number
US04868317

Reaction notes

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