Potassium Hydroxide → HCID 3516602, compound

HRID 1591004Notes

Reaction equation

HRID 1591004 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1(C(C2[C:22]([CH2:23][O:24][CH2:25][C:26]3[C:31](C4C(=CC=C(O)C=4)O)=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:20]=[CH:19][CH:18]=2)=CC(=CC=1)O)O.[OH-:40].[K+]>CS(C)=O>[CH2:25]([O:24][C:23]1[CH:18]=[CH:19][C:20]([O:40][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:21][CH:22]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 79040Ethyl 2-bromopropionateHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 3516602HCID 3516602, compoundYield 197.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 2-bromopropionate (36.2 g) and hydroquinone monobenzyl ether (40.0 g) were dissolved in dry dimethyl sulfoxide (100 ml), and pulverized potassium hydroxide (11.2 g) was added to the resultant solution. After stirring at room temperature for 20 hours, the reaction mixture was poured into ice-water (500 ml) and extracted with ethyl acetate (500 ml ×2). The extract was washed with 1 N hydrochloric acid, water, and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and the residue obtained by evaporation of the solvent under a reduced pressure was purified by medium pressure column chromatography using silica gel, to obtain ethyl 2-(4-benzyloxyphenoxy)propionate (57.3 g).

Workup

  1. extractionextracted with ethyl acetate (500 ml ×2)
  2. washThe extract was washed with 1 N hydrochloric acid, water, and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation of the solvent under a reduced pressure
  5. customwas purified by medium pressure column chromatography

Sources & evidence

ORD record
ord-534ca1c645834d4da8cf8981137edc4d
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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