Toluene → HCID 68578624, compound

HRID 644797Notes

Reaction equation

HRID 644797 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[N:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1C.[C:14]1(C)C=CC=CC=1>>[Br-:1].[OH:5][CH2:4][CH2:3][CH2:2][N+:6]1[CH:7]=[CH:8][C:9]([CH3:14])=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 3

HCID 1140TolueneHCID 79372,6-LutidineHCID 123083-Bromo-1-propanol

Product 1

HCID 68578624HCID 68578624, compound

Procedure

3-Bromopropanol (3,5 equivalents) was dissolved in some toluene in a round-bottomed flask flushed with nitrogen. Then, lutidine (1 equivalent) was added and the mixture was heated to reflux. After several hours, an off-white product appeared in the flask as a sticking solid. The reaction was stopped after 18 hours. The solvent was removed under the reduced pressure and ether was added to precipitate out the solids. After washing with ether, the product as off-white powders were dried. The yield of the reaction is 83%. The product is soluble in acetone, methanol and acetonitrile but not in diethyl ether. 1H NMR (CDCl3, 200 MHz): δ 2.24 (m, 2H), 2.61 (s, 3H), 3.03(s, 3H), 3.70 (t, 2H, J=4.86), 5.14 (t, 2H, J=7.26), 7.67 (s, 1H), 7.81(d, 1H, J=6.06), 9.65 (d, 1H, J=6.52); IR (CHCl3, cm−1): 1642 (C═C) (C═N), 3432 (O—H).

Workup

  1. customflushed with nitrogen
  2. temperaturethe mixture was heated to reflux
  3. waitAfter several hours
  4. customThe solvent was removed under the reduced pressure and ether
  5. additionwas added
  6. customto precipitate out the solids
  7. washAfter washing with ether
  8. dry with materialthe product as off-white powders were dried

Sources & evidence

ORD record
ord-f3d8e82a6dee4fc492b0dcd786f7e94a
Source dataset
uspto-grants-2010_04
Patent number
US07700780B2

Reaction notes

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