Water → Benzene, 1-methoxy-4-nitro-2-(2-propynyloxy)-

HRID 1881363Notes

Reaction equation

HRID 1881363 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C([O-])([O-])=O.[K+].[K+].[CH2:19](Cl)[C:20]#[CH:21].O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[O:12][CH2:21][C:20]#[CH:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 3448141Benzene, 1-methoxy-4-nitro-2-(2-propynyloxy)-Yield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

2-methoxy-5-nitrophenol (6.0 g, 35 mmol) and K2CO3 (6.5 g, 43 mmol) were stirred in acetone (200 mL) for 30 min and then propargyl chloride (6 mL, excess) was added to the suspension and heated at 65° C. overnight. After cooled to room temperature, water was added and the reaction mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water and brine and dried over Na2SO4. Recrystallization of the crude product in MeOH/EtOAc gave the title product as a white solid (6.4 g, 88%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe reaction mixture was extracted with EtOAc (100 mL×3)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customRecrystallization of the crude product in MeOH/EtOAc

Sources & evidence

ORD record
ord-4c6195d6def743a3aa0341bba27e184c
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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