Hydrochloric Acid → 4-{2-[4-(Hydroxymethyl)phenyl]hydrazinylidene}cyclohexa-2,5-dien-1-one
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[N:10]([O-])=O.[Na+].Cl.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC([O-])=O.[Na+]>CCO.O.CCO>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([N:1]=[N:10][C:18]2[CH:19]=[CH:20][C:15]([OH:21])=[CH:16][CH:17]=2)=[CH:3][CH:4]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
4-Aminobenzyl alcohol (0.36 g, 2.92 mmol) and NaNO2 (0.22 g, 3.21 mmol) were dissolved in 7.5 mL EtOH:water (1.5:1), added to 2 N HCl solution (4.5 mL) and stirred at 0° C. for 1 hour. Phenol (0.275 g, 2.92 mmol) in EtOH was added followed by NaOAc (0.15 g) at 0° C. and stirred for 6 hours at room temperature. Reaction mixture was quenched with saturated sodium bicarbonate solution (150 mL) and extracted with DCM. The organic layer was washed with water (200 mL), brine (950 mL), and dried over Na2SO4. Solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc:n-hexane 4:6) to obtain compound 1. Yield: 0.473 g (71%). 1H NMR and mass-spectrum data are in good agreement with previously published results.27
Workup
- stirringstirred for 6 hours at room temperature
- customReaction mixture
- customwas quenched with saturated sodium bicarbonate solution (150 mL)
- extractionextracted with DCM
- washThe organic layer was washed with water (200 mL), brine (950 mL)
- dry with materialdried over Na2SO4
- customSolvents were evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (EtOAc:n-hexane 4:6)
Sources & evidence
- ORD record
- ord-c641ca6872164758917766c12a10343c
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09345781B2
Reaction notes
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