Hydroquinone → HCID 13341673, compound
Reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:22][CH2:23][CH2:24][O:25][C:26](=[O:30])[CH:27](Br)[CH3:28])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([O:22][CH2:23][CH2:24][O:25][C:26](=[O:30])[CH:27]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH3:28])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
12.1 g of hydroquinone were dissolved in 60 ml of dry dimethylformamide, 31.7 g of potassium carbonate were added thereto in a slow stream of nitrogen, and then the mixture was heated to 90° to 95° C. for one hour with stirring. The mixture was cooled to 60° C., and to it were added dropwise 28.7 g of 2-benzyloxyethyl-2-bromopropionate. The reaction mixture was heated at 90° C. for two hours. After cooling the reaction solution to room temperature, it was poured into ice-water and adjusted to pH7, then extracted with 100 ml of toluene. The toluene layer was dried and filtered, and then toluene was removed under reduced pressure. The colorless oily product of 2-benzyloxyethyl-2-(4-hydroxyphenoxy)propionate was obtained in a yield of 24.6 g. (nD21.5 1.5390)
Workup
- temperaturein a slow stream of nitrogen, and then the mixture was heated to 90° to 95° C. for one hour
- temperatureThe reaction mixture was heated at 90° C. for two hours
- temperatureAfter cooling the reaction solution to room temperature
- extractionextracted with 100 ml of toluene
- dry with materialThe toluene layer was dried
- filtrationfiltered
- customtoluene was removed under reduced pressure
Sources & evidence
- ORD record
- ord-07606a03b3284f1a96af9e3b736cd24b
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04584396
Reaction notes
Loading…