(1,1'-Biphenyl)-2-ol → HCID 4539764, compound

HRID 2269638Notes

Reaction equation

HRID 2269638 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 7748Ethyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 4539764HCID 4539764, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 10 ml of acetonitrile, 1.0 g of o-phenylphenol and 1.29 ml of ethyl bromoacetate were added in the presence of 1.76 ml of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) and the resultant mixture was refluxed for 8 hr. The reaction mixture was treated similarly to that in Example 28 (Process2) to give 1.46 g of ethyl o-phenylphenoxyacetate. The ester was dissolved in 30 ml of ethanol, mixed with 10.8 ml of 1N—NaOH aqueous solution and stirred for 12 hr. The reaction mixture was evaporated under reduced pressure, acidified by the addition of 1N-HCl and extracted with ethyl acetate. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure and o-phenylphenoxyacetic acid was crystallized as DCHA salt from ether with the yield of 1.59 g.

Workup

  1. additionThe reaction mixture was treated similarly to that in Example 28 (Process2)

Sources & evidence

ORD record
ord-50b3635390c44745beab020892ff26c9
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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