Benzyl Bromide → HCID 14495469, compound

HRID 620091Notes

Reaction equation

HRID 620091 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. After the reaction, 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 the objective ester compound of the following formula. (yield: 76%) ##STR44##

Workup

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

Sources & evidence

ORD record
ord-a9cf72b307ac4fb98fb98631b4405e64
Source dataset
uspto-grants-1989_04
Patent number
US04818807

Reaction notes

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