Water → HCID 21804318, compound

HRID 2379518Notes

Reaction equation

HRID 2379518 reaction equation
O[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].O>O1CCOCC1.S(=O)(=O)(O)O>[CH2:13]([C:9]1[CH:8]=[C:7]([C:2](=[CH2:6])[C:3]([OH:5])=[O:4])[CH:12]=[CH:11][CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 962WaterHCID 18957450HCID 18957450, compound

Product 1

HCID 21804318HCID 21804318, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

136 g (0.531 mol) of 2-hydroxy-2-(3-benzyl-phenyl)-propanoic acid (product from Example 11) are refluxed in a mixture of 3 l of dioxane and 180 ml of concentrated sulphuric acid. Water is added to the mixture which has been concentrated to approximately 500 ml and the mixture is extracted three times with ether. After drying the organic phases using saturated NaCl and magnesium sulphate, a brown oil remains, which is purified by filtration on 1 kg of silica gel (ethyl acetate/cyclohexane 5:1). Yield: 83 g (66%).

Workup

  1. concentrationhas been concentrated to approximately 500 ml
  2. extractionthe mixture is extracted three times with ether
  3. customAfter drying the organic phases
  4. filtrationa brown oil remains, which is purified by filtration on 1 kg of silica gel (ethyl acetate/cyclohexane 5:1)

Sources & evidence

ORD record
ord-79ce2c217acd4f949d2b466d625bae27
Source dataset
uspto-grants-1994_11
Patent number
US05362907

Reaction notes

Loading…