Potassium Hydroxide → HCID 3516602, compound
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]=1Participants
5
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 1N 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
- extractionextracted with ethyl acetate (500 ml×2)
- washThe extract was washed with 1N hydrochloric acid, water, and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customthe residue obtained by evaporation of the solvent under a reduced pressure
- customwas purified by medium pressure column chromatography
Sources & evidence
- ORD record
- ord-4a39bfdbbb044c1ebb1fbdd0514296d7
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04976773
Reaction notes
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