Hydrochloric Acid → HCID 22237768, compound

HRID 1743086Notes

Reaction equation

HRID 1743086 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][CH3:18])[CH:5]=[CH:4][C:3]=1[N+:19]([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][CH3:18])[CH:5]=[CH:4][C:3]=1[NH2:19]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 22237767HCID 22237767, compound

Product 1

HCID 22237768HCID 22237768, compoundYield 76%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
75 °C

Procedure

The mixture of crude 2-methyl-4-decyloxynitrobenzene (90 g, 0.294 mol), methanol (246 mL), concentrated hydrochloric acid (159 mL) and dioxane (70 mL) was heated to 75° C. Iron powder (49.9 g, 0.89 mol) was added in small portions with vigorous stirring. After the addition was complete the reaction mixture was stirred at 75° C. for another 20 minutes and poured warm into water (3 L), stirred for 30 minutes and the pH adjusted to 11.0 by addition of aqueous potassium carbonate solution. Dichloromethane (3 L) was added and the mixture was stirred intensively for 1 hour. The layers were separated and the organic layer dried over sodium sulfate and passed through a thin pad of silica gel. The solvent was evaporated to dryness to give a brown oil (58.5 g, 0.22 mol, 76% yield).

Workup

  1. additionAfter the addition
  2. additionpoured
  3. stirringstirred for 30 minutes
  4. stirringthe mixture was stirred intensively for 1 hour
  5. customThe layers were separated
  6. dry with materialthe organic layer dried over sodium sulfate
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-cd8b38f4ac524b0fb04c7dc3f08c9ae5
Source dataset
uspto-grants-2006_03
Patent number
US07008759B2

Reaction notes

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