Hydrochloric Acid → HCID 22237766, compound

HRID 1353140Notes

Reaction equation

HRID 1353140 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:5]=[CH:4][C:3]=1[N+:27]([O-])=O.CO.Cl.C(=O)([O-])[O-].[K+].[K+]>[Fe].ClCCl.O.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:5]=[CH:4][C:3]=1[NH2:27]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 22237764HCID 22237764, compound

Product 1

HCID 22237766HCID 22237766, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

The mixture of crude 2-methyl-4-octadecyloxynitrobenzene (30 g, ca. 0.065 mol), methanol (55 mL), concentrated hydrochloric acid (40.5 mL) and dioxane (50 mL) was heated to 85° C. Iron powder (11.2 g, 0.20 mol) was added in small portions with intensive stirring. After the addition was complete the reaction mixture was stirred at 85° C. for another 3 hours and poured warm into water (800 mL), stirred for 30 minutes and the pH adjusted to 10.0 by addition of aqueous potassium carbonate solution. Dichloromethane (1.0 L) was added and mixture was stirred intensively for 1 hour. The layers were separated and the organic layer was washed with water (2×500 mL) and dried over sodium sulfate. The solvent was evaporated to give an oil (20 g, 0.053 mol, 82% yield), which solidified on standing.

Workup

  1. additionAfter the addition
  2. additionpoured
  3. stirringstirred for 30 minutes
  4. stirringmixture was stirred intensively for 1 hour
  5. customThe layers were separated
  6. washthe organic layer was washed with water (2×500 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-af4eef3e17984f56ad3a17ca739c3224
Source dataset
uspto-grants-2007_05
Patent number
US07220868B2

Reaction notes

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