4-Toluenesulfonyl chloride → (2Z)-3-(2-cyanophenyl)prop-2-enoic acid
Reaction equation
[N:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13])=O.C1(C)C=CC(S(Cl)(=O)=[O:21])=CC=1.[OH-].[Na+]>C1COCC1.O>[C:3]([C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:6]=[CH:5]\[C:4]([OH:13])=[O:21])#[N:1]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution of 1-nitrosonaphthalen-2-ol (5 g) dissolved in THF (30 mL) was treated with p-toluenesulfonyl chloride (6.61 g) under nitrogen. The resulting mixture was stirred at 20° C. for 1 h. The mixture was treated with a solution of sodium hydroxide (4.04 g) in water (30 mL) dropwise over 30 min to keep temperature below 25° C. The reaction mixture was diluted with water (200 mL), and extracted with diethyl ether (200 mL) (discarded). The aqueous layer was acidified with 2M HCl, extracted with ethyl acetate (200 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with 50% diethyl ether in isohexane to give the subtitle compound as a solid (4.75 g).
Workup
- customtemperature below 25° C
- extractionextracted with diethyl ether (200 mL) (discarded)
- extractionextracted with ethyl acetate (200 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe residue was triturated with 50% diethyl ether in isohexane
Sources & evidence
- ORD record
- ord-e27be86664be4e5b8c0eeb7d16fe2636
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299246B2
Reaction notes
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