Hydrochloric Acid → HCID 21187686, compound

HRID 1637077Notes

Reaction equation

HRID 1637077 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1(O)[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21187684HCID 21187684, compound

Product 1

HCID 21187686HCID 21187686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-(2-Methoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol (100 mg, 0.379 mmol) in 10 mL THF was added HCl (1.4 mL 6M, 8.4 mmol). The solution was heated to 80° C. for 45 min, then poured onto saturated sodium bicarbonate and extracted with ethylacetate. The combined organic layers were washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. The crude material was passed through silica (dichloromethane/3% methanol as eluent) to give 4-(2-Methoxy-phenyl)-cyclohex-3-enone

Workup

  1. extractionextracted with ethylacetate
  2. washThe combined organic layers were washed with saturated sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea8c9840c3bd4426b50f31bf9a4ed0cc
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

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