Water → 4'-(Benzyloxy)[1,1'-biphenyl]-4-carboxylic acid

HRID 976283Notes

Reaction equation

HRID 976283 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.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 147447934'-(Benzyloxy)[1,1'-biphenyl]-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

4'-hydroxy 4-biphenylcarboxylic acid (5.0 g) was added to a stirred suspension of sodium hydride (60% w/w dispersion in mineral oil, 2.34 g) in dry dimethylformamide (45 ml) whilst maintaining the temperature of the reaction mixture below 10° C. The reaction mixture was stirred at 10° C. for 20 minutes. A solution of benzyl bromide (8.4 g) in dry dimethylformamide (10 ml) was added over a period of 10 minutes. The reaction mixture was stirred at 70° C. for 2 hours and the mixture was then poured into cold water (900 ml) to precipitate a solid. The solid was collected by filtration, washed with water (3×200 ml) and added to a mixture of 2M aqueous sodium hydroxide solution (100 ml) and ethanol (100 ml). The mixture was stirred at 100° C. for 12 hours. The ethanol was removed by evaporation and the aqueous residue taken to pH 1.0 by the addition of 12M aqueous hydrochloric acid solution to precipitate a solid. The solid was collected by filtration, washed with water (3×100 ml), ethyl acetate (3×100 ml) and dried to give 4'-benzyloxy-4-biphenylcarboxylic acid (100% yield) as a colourless solid, m.p. >300° C.; m/z 304 (M).

Workup

  1. temperaturewhilst maintaining the temperature of the reaction mixture below 10° C
  2. stirringThe reaction mixture was stirred at 70° C. for 2 hours
  3. customto precipitate a solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (3×200 ml)
  6. additionadded to a mixture of 2M aqueous sodium hydroxide solution (100 ml) and ethanol (100 ml)
  7. stirringThe mixture was stirred at 100° C. for 12 hours
  8. customThe ethanol was removed by evaporation
  9. additionthe aqueous residue taken to pH 1.0 by the addition of 12M aqueous hydrochloric acid solution
  10. customto precipitate a solid
  11. filtrationThe solid was collected by filtration
  12. washwashed with water (3×100 ml), ethyl acetate (3×100 ml)
  13. customdried

Sources & evidence

ORD record
ord-5bd4e2c9fac745a28303f62e73a52191
Source dataset
uspto-grants-1997_03
Patent number
US05612352

Reaction notes

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