Methylparaben → Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1F)#[N:2].[OH:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:14]([O:13][C:11](=[O:12])[CH2:10][C:5]1[CH:6]=[CH:7][C:8]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)=[C:3]([C:1]#[N:2])[CH:4]=1)([CH3:17])([CH3:16])[CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 125 °C
Procedure
tert-Butyl 2-(3-cyano-4-fluorophenyl)acetate (2.6 g, 11.1 mmol) and methyl 4-hydroxybenzoate (3.36 g, 22.1 mmol) were diluted with DMSO (22 mL) followed by the addition of potassium carbonate (1.83 g, 13.3 mmol). The reaction mixture was heated to 125° C. and stirred for 5 hours. The reaction mixture was diluted with ethyl acetate and 10% aqueous sodium carbonate. The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate two more times followed by water and brine. The organic material was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40M column eluting with hexanes:ethyl acetate (9:1) to yield methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate (2.65 g, 65.3% yield) as a clear oil.
Workup
- customThe layers were separated
- washthe organic layer was washed with 10% aqueous sodium carbonate two more times
- dry with materialThe organic material was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe material was purified
- washeluting with hexanes:ethyl acetate (9:1)
Sources & evidence
- ORD record
- ord-5681aace3c8c4f9990e783c66cb9cc32
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183289B2
Reaction notes
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