Acetone → HCID 86642600, compound

HRID 1925796Notes

Reaction equation

HRID 1925796 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:17][CH3:18])[C:12]=1[O:13][CH2:14][C:15]#[CH:16])[CH:8]=O.[CH3:19][C:20]([CH3:22])=[O:21].Cl>C(OCC)(=O)C.CCCCCC.C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:8]=[CH:19]/[C:20](=[O:21])[CH3:22])[CH:10]=[C:11]([O:17][CH3:18])[C:12]=1[O:13][CH2:14][C:15]#[CH:16]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4771126HCID 4771126, compound

Product 1

HCID 86642600HCID 86642600, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To an aqueous 10% sodium hydroxide solution (4.3 mL, 1.0 M) was added slowly dropwise a mixture of an ethanol (4.3 mL, 1.0 M) solution of 3,5-dimethoxy-4-prop-2-ynyloxybenzaldehyde (0.95 g, 4.3 mmol) and acetone (1.27 mL, 17.3 mmol), and the resultant mixture was stirred for 1 hour at room temperature, followed by addition of 10% hydrochloric acid. The mixture was then extracted with ethyl acetate, washed with saturated saline, dried over magnesium sulfate, and evaporated under reduced pressure to give a residue which was subjected to silica gel chromatography. A white solid (605 mg, 54%) was obtained from an ethyl acetate/hexane eluent (1:1 v/v).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washwashed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto give a residue which

Sources & evidence

ORD record
ord-b492e8842d4e4433a8641985728b0bcf
Source dataset
uspto-grants-2012_05
Patent number
US08178727B2

Reaction notes

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