Dimethyl Sulfate → 5-[3-Hydroxy-4-(2-methoxybenzoyl)-2-propylphenoxy]pentanenitrile
Reaction equation
[OH:1][C:2]1[C:3]([CH2:24][CH2:25][CH3:26])=[C:4]([CH:12]=[CH:13][C:14]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[N:11].[C:27](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(=O)CC>[OH:1][C:2]1[C:3]([CH2:24][CH2:25][CH3:26])=[C:4]([CH:12]=[CH:13][C:14]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:27])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[N:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Five grams of 5-[3-hydroxy-4-(2-hydroxybenzoyl)-2-propylphenoxy]pentanenitrile, 11.7 g of potassium carbonate, and 1.42 ml of dimethyl sulfate in 50 ml of 2-butanone were stirred at reflux for approximately 18 hours. After cooling to 25° C., the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with one volume of water and one volume of a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated to dryness leaving a yellow oil which crystallized on standing. Recrystallization from ethyl acetate/hexane provided 4.38 g of the desired title product, m.p. 85°-86.5° C.
Workup
- temperatureat reflux for approximately 18 hours
- customthe mixture was partitioned between ethyl acetate and water
- customThe organic layer was separated
- washwashed with one volume of water and one volume of a saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- customleaving a yellow oil which
- customcrystallized
- customRecrystallization from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-16e7fc88054447159a7de497779148d0
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04801616
Reaction notes
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