Monobenzone → 1-Benzyloxy-4-(2-phenethyloxyethoxy)benzene
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
10 g of 4-benzyloxyphenol in 120 ml of dimethylformamide were treated with 2.4 g of a 50% sodium hydride dispersion in mineral oil and the mixture was stirred for 5 minutes. 12.2 g of 2-(2-phenylethoxy)ethyl methanesulfonate [prepared as described in Example 1(a)] were added and the mixture was heated at 60° C. for 0.5 hour with stirring. The mixture was evaporated to dryness and the residue was partitioned between 2N sodium hydroxide and ethyl acetate. The organic phase was separated, washed well with water, dried over sodium sulfate, filtered and evaporated. The residue was recrystallized from methylcyclohexane to give 16.1 g (93%) of 1-benzyloxy-4-(2-phenethyloxyethoxy)benzene of melting point 46°-49° C.
Workup
- stirringwith stirring
- customThe mixture was evaporated to dryness
- customthe residue was partitioned between 2N sodium hydroxide and ethyl acetate
- customThe organic phase was separated
- washwashed well with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was recrystallized from methylcyclohexane
Sources & evidence
- ORD record
- ord-dbb226c043e54d2d8a5acf57d9efecc7
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04649160
Reaction notes
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