1-Bromooctane → 4'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acid

HRID 1387253Notes

Reaction equation

HRID 1387253 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.[OH-].[Na+]>>[CH2:1]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acid

Conditions

Temperature
70 °C

Procedure

n-Octyl bromide (0.102 mol) is added to a solution of 4-(4-hydroxyphenyl)benzoic acid (0.102 mol) and 2.5N sodium hydroxide (0.102 mol) and the mixture stirred at 70° C. for a period of 18 hours. The reaction mixture is allowed to cool and then acidified to pH 3 and partitioned between ethyl acetate and water. The organic phase is washed with water and brine and the solvent then removed to obtain the 4′-n-octyloxy[1,1′-biphenyl]-4-ylcarboxylic acid, C21H23O3, M.W. 326.4.

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase is washed with water and brine
  4. customthe solvent then removed

Sources & evidence

ORD record
ord-9f358419aa9f41d2a2b10073792df385
Source dataset
uspto-grants-2001_07
Patent number
US06268338B1

Reaction notes

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