Water → HCID 67235564, compound

HRID 1505316Notes

Reaction equation

HRID 1505316 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:18][CH3:19].O.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 672363822-Methoxy-1-methyl-4-(4-nitrophenoxy)benzene2×

Product 1

HCID 67235564HCID 67235564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-2-(methyloxy)-4-[(4-nitrophenyl)oxy]benzene (Intermediate 19, 1.43 g) in tetrahydrofuran (65 mL)/water (32.5 mL) iron (1.540 g, 27.6 mmol) and then ammonium chloride (1.475 g, 27.6 mmol) were added and the reaction mixture was stirred for 5 hours at room temperature. The catalyst was filtered off and the solution was diluted with a saturated solution of Na2CO3 (10 mL) and extracted with ethyl acetate (2 times 60 mL). Combined organic layers were dried over sodium sulphate, filtered and evaporated to the title compound (1.25 g) as a brown/red solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe solution was diluted with a saturated solution of Na2CO3 (10 mL)
  3. extractionextracted with ethyl acetate (2 times 60 mL)
  4. dry with materialCombined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to the title compound (1.25 g) as a brown/red solid

Sources & evidence

ORD record
ord-5bfc12b90ce54a438f0fdd5a44317135
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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