Acetic Acid → 2-(p-Bromophenyl)-1-(2-pyridyl)-2-propanol

HRID 461920Notes

Reaction equation

HRID 461920 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].C(O)(=O)C>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])([CH3:9])[CH2:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[CH:4][CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:9])=[CH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7466p-BromoacetophenoneHCID 79752-Methylpyridine

Product 2

HCID 205601152-(p-Bromophenyl)-1-(2-pyridyl)-2-propanolYield 63%HCID 541806622-[2-(4-Bromophenyl)prop-1-en-1-yl]pyridineYield 26%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(p-Bromophenyl)-1-(2-pyridyl)-2-propanol is prepared from p-bromoacetophenone and 2-picoline according to the method of Villani, et al., J. Med. Chem., 13, 359 (1970) in 63% yield. This alcohol (129.1 g.) is dehydrated by heating in 1150 ml. of acetic acid-12N hydrochloric acid (3:1) at reflux temperature for 4 hr. The mixture is evaporated in vacuo, made basic with concentrated ammonium hydroxide, and extracted with ethyl acetate. The ethyl acetate extract is washed with water and brine, dried over sodium sulfate, and evaporated to give a dark brown oil. A solution of the oil in benzene is passed through a column of silica gel. Evaporation of the eluate gave 46.4 g (26% yield) of crystalline 2-(p-bromophenyl)-1-(2-pyridyl)propene, m.p. 71.5°-73.5° C. (corr.).

Workup

  1. temperatureby heating in 1150 ml
  2. customThe mixture is evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give a dark brown oil
  9. customEvaporation of the eluate

Sources & evidence

ORD record
ord-48ec34ba24e749ef9806e5eb6e15a92f
Source dataset
uspto-grants-1977_12
Patent number
US04064254

Reaction notes

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