Water → 1-[(3-Phenoxyphenyl)methyl]pyridin-1-ium bromide

HRID 918121Notes

Reaction equation

HRID 918121 reaction equation
C1(C)C=CC=CC=1[C:7]1[CH:8]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3C=CC=CC=3C)[CH:15]=2)[CH:10]=[CH:11][CH:12]=1.O(C1C=C(C=CC=1)C[Br:39])C1C=CC=CC=1.C1(C)C(C)=CC=CC=1.O.[N:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>>[Br-:39].[O:13]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][N+:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:9]1[CH:8]=[CH:7][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 7237O-XyleneHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 70567605HCID 70567605, compound

Product 1

HCID 215229631-[(3-Phenoxyphenyl)methyl]pyridin-1-ium bromide

Procedure

52.6 g of the brominated product of m-tolylphenyl ether containing 26.3 g of 3-phenoxybenzyl bromide was added to a mixed solution of 100 ml of xylene and 50 ml of water, and then 11.9 g of pyridine was added thereto. The mixture was heated to 70° to 75°C, kept at the same temperature for 3 hours while stirring and then cooled to room temperature (about 20° - 30°C). The lower aqueous layer which separated was removed, washed with a small amount of xylene, evaporated and then dried under a reduced pressure to obtain 34.5 g of colorless, crystalline 3-phenoxybenzyl pyridinium bromide (m.p. 120° - 121°C).

Workup

  1. temperatureThe mixture was heated to 70° to 75°C
  2. customThe lower aqueous layer which separated
  3. customwas removed
  4. washwashed with a small amount of xylene
  5. customevaporated
  6. customdried under a reduced pressure

Sources & evidence

ORD record
ord-915e94ed747349f0bd38ae61259ada56
Source dataset
uspto-grants-1976_07
Patent number
US03969393

Reaction notes

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