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

HRID 1662370Notes

Reaction equation

HRID 1662370 reaction equation
[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:5]2C(=O)OC(C)(C)[O:7][C:6]2=[O:14])[CH2:3][CH2:2]1>CN(C=O)C.O.O>[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:5][C:6]([OH:14])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 1

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

Product 1

HCID 577059733-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

5-(Cyclopropyl(3-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 66.6T (14.64 g, 50.43 mmol) in DMF/water (10/1) (220 mL) was heated at 90° C. overnight. The reaction was then diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 66.6U as a clear oil (10.40 g, 100%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1e07a73d893f4954978babcfbfc5f2ad
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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