Hydrochloric Acid → 5-[Cyclopropyl(3-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 709595Notes

Reaction equation

HRID 709595 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH:5]=[C:6]1[C:11](=[O:12])[O:10][C:9]([CH3:14])([CH3:13])[O:8][C:7]1=[O:15].[CH:19]1([Mg]Br)[CH2:21][CH2:20]1.Cl.O>C1COCC1>[CH:19]1([CH:5]([C:4]2[CH:16]=[CH:17][CH:18]=[C:2]([OH:1])[CH:3]=2)[CH:6]2[C:7](=[O:15])[O:8][C:9]([CH3:14])([CH3:13])[O:10][C:11]2=[O:12])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6053805-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418630HCID 178418630, compound

Product 1

HCID 577059545-[Cyclopropyl(3-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (5-(3-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (65.0 g) in THF (1.30 L) was added dropwise a 10% solution of cyclopropylmagnesium bromide in THF (2.20 kg) at −11° C. to −1° C. over 1.6 hr, and the mixture was stirred at room temperature for 2 hr. 1N Hydrochloric acid was added to the reaction mixture at 2° C. to 17° C. to adjust the solution to pH 3. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (76.0 g) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2f8d404935ce41059473bf6e627f74c8
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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