4-Hydroxybiphenyl → HCID 15675493, compound

HRID 974025Notes

Reaction equation

HRID 974025 reaction equation
[C:1]1([C:16]2C=CC=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([O:7]CCCCCCC#N)=CC=1.BrCCCCCCC#N.[C:31]1([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-:44].[Na+]>C(O)CO.O.C(O)(=O)C.O.CO>[C:37]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:38]=[CH:39][C:40]([O:43][CH2:18][CH2:17][CH2:16][CH2:1][CH2:6][CH2:5][C:4]([OH:44])=[O:7])=[CH:41][CH:42]=1

Participants

9

Reactant 4

HCID 71034-HydroxybiphenylHCID 14798Sodium HydroxideHCID 88737Heptanenitrile, 7-bromo-HCID 15675492HCID 15675492, compound

Product 1

HCID 15675493HCID 15675493, compoundYield 97%

Reagents, catalysts & solvents 4

HCID 174Ethylene GlycolSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

By the method of Example 34, 7-([1,1'-biphenyl]-4-yloxy)-heptanenitrile was prepared from 7-bromoheptanenitrile and 4-phenylphenol, as shiny flakes from water-methanol, mp 78°-79° C. This material (3.0 g, 10.7 mmol) was heated in ethylene glycol (100 g) containing water (33 ml) and NaOH (10 g). After four hours at reflux, during which the nitrile dissolved and a solid formed, the mixture was cooled, diluted with water (400 ml), and acidified with acetic acid (100 ml). The precipitate was collected by filtration, and dried in vacuo to provide 7-([1,1'-biphenyl]-4-yloxy)heptanoic acid as a white solid (3.1 g 97% yield).

Workup

  1. dissolutiondissolved
  2. customa solid formed
  3. temperaturethe mixture was cooled
  4. filtrationThe precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0039760ae81f407b828110c00bac31a9
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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