Hydrochloric Acid → HCID 73052801, compound

HRID 1503079Notes

Reaction equation

HRID 1503079 reaction equation
[O:1]=[C:2]([CH3:11])[CH2:3][C:4]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5]1.[C:12]1(C)C=C(C)C=C(C)C=1.Cl>CO>[CH3:12][O:9][C:8](=[O:10])[CH2:7][C:4]1([CH2:3][C:2](=[O:1])[CH3:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7947MesityleneHCID 69098014HCID 69098014, compound

Product 1

HCID 73052801HCID 73052801, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.9 g crude [1-(2-oxo-propyl)-cyclopropyl]-acetic acid (31 mmole) in 73.5 ml methanol are added 1 ml of mesitylene (GC standard) and 2.5 ml of conc. hydrochloric acid. The mixture is heated to reflux for 1 hour and then concentrated to dryness. 40 ml of water are added to the residue and the resulting mixture is extracted with 100 ml of methyl tert-butyl ether in two portions. The combined organic phases are concentrated to dryness. The resulting crude product is directly used in the next step (spiro[2.5]octane-5,7-dione).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated to dryness
  4. addition40 ml of water are added to the residue
  5. extractionthe resulting mixture is extracted with 100 ml of methyl tert-butyl ether in two portions
  6. concentrationThe combined organic phases are concentrated to dryness

Sources & evidence

ORD record
ord-f2904c38a35b45808e920eb9c22d68aa
Source dataset
uspto-grants-2015_12
Patent number
US09212120B2

Reaction notes

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