Sodium Hydroxide → 3,4-Diaminophenol
Reaction equation
[Na].[NH2:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[CH:7][C:8]=1[NH2:9].NC1C=CC(OC)=CC=1N.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[NH2:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[CH:7][C:8]=1[NH2:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
3,4-Diamino-phenol sodium salt. To a 200-mL, round-bottomed flask containing a solution of 1,2-diamino-4-methoxy-benzene (0.50 g, 3.6 mmol, Avocado) in CH2Cl2 (5 mL) was added dropwise a solution of BBr3 in CH2Cl2 (15 mL, 15 mmol, 1.0 M, Aldrich) with stirring at −30° C. under N2. The mixture was stirred at room temperature for 5 h and quenched with ice water (25 mL) by cooling with and ice bath. The mixture was basified to pH 9 with 1 N NaOH and extracted with water (2×8 mL). The combined aq. extracts containing the title compound were used directly in the next reaction. A small portion of the aq. solution was neutralized with 1 N NaOH to give an analytical sample of 3,4-diamino-phenol. MS (ESI, pos. ion) m/z: 125 (M+1).
Workup
- stirringThe mixture was stirred at room temperature for 5 h
- customquenched with ice water (25 mL)
- temperatureby cooling with and ice bath
- extractionextracted with water (2×8 mL)
- additionThe combined aq. extracts containing the title compound
- customwere used directly in the next reaction
Sources & evidence
- ORD record
- ord-566ca994f8084cd9ab49a74a96c73580
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148221B2
Reaction notes
Loading…