Methanol → HCID 85711141, compound

HRID 1075407Notes

Reaction equation

HRID 1075407 reaction equation
[CH2:1]([N:9]([CH3:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:19][CH2:20][CH2:21][CH2:22][Cl:23].CO.C(C(C)=O)C>CCCCCC>[Br-:19].[Cl:23][CH2:22][CH2:21][CH2:20][N+:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 6569Methyl Ethyl KetoneHCID 80061-Bromo-3-chloropropaneHCID 78202N-Methyldioctylamine

Product 1

HCID 85711141HCID 85711141, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
65 °C

Procedure

A one-liter, 3-necked, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged with N,N-dioctylmethylamine (202.48 grams, 0.79 moles), 1-bromo-3-chloropropane (124.8 grams, 0.79 moles) and methanol (250 mL). Reaction was maintained at 65° C. for two days. Methanol was removed by rotary evaporation under reduced pressure to yield an oil. To the oil was added ethylmethylketone (50 mL) and hexane (200 mL) causing a white solid to slowly form. The solvent was decanted from the mixture. The remaining solid was washed with hexane (50 mL) two times. The solid was placed in a vacuum oven at 35° C. for 24 hours. Yield 259 grams of a waxy solid (0.625 moles, 79%).

Workup

  1. customA one-liter, 3-necked, round-bottomed flask equipped with air condensers
  2. customReaction
  3. customMethanol was removed by rotary evaporation under reduced pressure
  4. customto yield an oil
  5. customto slowly form
  6. customThe solvent was decanted from the mixture
  7. washThe remaining solid was washed with hexane (50 mL) two times

Sources & evidence

ORD record
ord-ae4f869c4bb54656812fb5f7b2ff1052
Source dataset
uspto-grants-1999_05
Patent number
US05900475

Reaction notes

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