Water → HCID 88746404, compound

HRID 1446892Notes

Reaction equation

HRID 1446892 reaction equation
[C:1]([CH:4]1[CH2:10][CH:9]2[CH:7]([C:8]2([CH3:12])[CH3:11])[CH:6]([O:13]C)[O:5]1)(=[O:3])[CH3:2].O.S(=O)(=O)(O)O>CC(C)=O>[OH:5][CH:4]([C:1](=[O:3])[CH3:2])[CH2:10][C@@H:9]1[C:8]([CH3:12])([CH3:11])[C@@H:7]1[CH:6]=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 20553531HCID 20553531, compound

Product 1

HCID 88746404HCID 88746404, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 50-ml flask was charged with 4-acetyl-2-methoxy-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane (10.1 mmol, 100% (1R,cis)), a 1:1 (v) mixture (20 ml) of water and acetone and concentrated sulphuric acid (1.5 mmol), sp. gr. 1.84. After stirring the contents of the flask for one hour at 20° C. the majority of acetone was distilled off at 1.3 kPa. The residue was extracted with two 10-ml portions of dichloromethane. The combined extract phases were washed with two 20-ml portions of a saturated aqueous solutions of sodium hydrogen carbonate and then with a 10%w aqueous solution (20 ml) of sodium chloride. The washed organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated from the dried organic phase at 1.3 kPa to leave a residue (1.6 g) containing 2-(2-hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde (100% (1R,cis), yield 86%).

Workup

  1. distillationwas distilled off at 1.3 kPa
  2. extractionThe residue was extracted with two 10-ml portions of dichloromethane
  3. extractionThe combined extract phases
  4. washwere washed with two 20-ml portions of a saturated aqueous solutions of sodium hydrogen carbonate
  5. dry with materialThe washed organic phase was dried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated from the dried organic phase at 1.3 kPa

Sources & evidence

ORD record
ord-96305b6e67284858976eb45f21a765cf
Source dataset
uspto-grants-1982_02
Patent number
US04314072

Reaction notes

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