Water → HCID 54395130, compound

HRID 384584

Reaction equation

HRID 384584 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[OH-].[Na+].O.[OH:9][C:10]([CH3:24])([CH3:23])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1)=[O:12]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC>[OH:9][C:10]([CH3:24])([CH3:23])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][CH2:1][CH:3]2[CH2:4][O:5]2)=[CH:15][CH:14]=1)=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 862662-Hydroxy-1-(4-(hydroxyethoxy)phenyl)-2-methyl-1-propanone

Product 1

HCID 54395130HCID 54395130, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Epichlorohydrin (24 g, 0.261 mol) is added to a mixture of 16.31 g (0.408 mol) of sodium hydroxide, 45 ml of water, and 0.761 g (2.24 mmol) of tetrabutylammonium hydrogen sulfate that is previously cooled in an ice-water bath for 20 minutes. To this mixture is added dropwise over 45 minutes with rapid stirring, a solution of 10.32 g (46.0 mmol) of 2-hydroxy-1-[4-(2-hydroxy-ethoxy)phenyl]-2-methylpropan-1-one in 95 ml of 1,2-dimethoxyethane. The reaction mixture is stirred overnight at room temperature. The aqueous layer is removed, and the organic layer is concentrated. Purification by flash chromatography on silica gel (1:1 heptane:ethyl acetate) affords 9.20 g (71% of theoretical yield) of the title compound, a pale yellow liquid.

Workup

  1. temperatureis previously cooled in an ice-water bath for 20 minutes
  2. additionTo this mixture is added dropwise over 45 minutes with rapid stirring
  3. customThe aqueous layer is removed
  4. concentrationthe organic layer is concentrated
  5. customPurification by flash chromatography on silica gel (1:1 heptane:ethyl acetate)
  6. customaffords

Sources & evidence

ORD record
ord-7c56b95367ff400fbe725bfb25a67097
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Linked notes

Loading…