Water → HCID 21997553, compound

HRID 1977275Notes

Reaction equation

HRID 1977275 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[O:19]([CH2:26][CH2:27][CH2:28][CH2:29]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CS(C)=O>[O:19]([CH2:26][CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[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 14798Sodium HydroxideHCID 70986(4-Bromobutoxy)benzeneHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 21997553HCID 21997553, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(4′-hydroxyphenyl)benzoic acid (4 g) and 1N sodium hydroxide (41 ml) in dimethyl sulfoxide (40 ml) was heated for 30 minutes at 85° C., then treated with 4-phenoxybutyl bromide (6.42 g) and heating continued for 8 hours. After cooling, the reaction was poured into water and adjusted to pH 2 and the resulting precipitate was collected, washed with water, and dried to give 4-[4′-(4-phenoxybutyloxy) phenyl]benzoic acid (6.7 g).

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. customthe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-66bb5874af52400a8d9fece67c961b81
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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