Benzyl Bromide → HCID 14495469, compound

HRID 620092Notes

Reaction equation

HRID 620092 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].C[N+](C)(C)C.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 60966Tetramethylammonium hydroxideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 14495469HCID 14495469, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.1 mol (21.4 g) of 4'-hydroxybiphenyl-4-carboxylic acid and 0.11 mol (19.9 g) of tetramethylammonium hydroxide (pentahydrate) in 200 ml of DMF was stirred for 2 hours. To this was then added 0.1 mol (17.1 g) of benzyl bromide and the mixture was stirred for 6 hours. The reaction solution was extracted with ether and the extract was dried and concentrated. The resulting crude product was purified by column chromatography to obtain 23.1 g of the objective ester compound of the following formula. (yield: 76%) ##STR98##

Workup

  1. extractionThe reaction solution was extracted with ether
  2. customthe extract was dried
  3. concentrationconcentrated
  4. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c328fa3b4b244a18b9882650e1425a44
Source dataset
uspto-grants-1989_04
Patent number
US04818807

Reaction notes

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