(1,1'-Biphenyl)-2-ol → (2-phenylphenyl) benzoate

HRID 1852297Notes

Reaction equation

HRID 1852297 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.C(N(CC)CC)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[C:21]([O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 408844(2-phenylphenyl) benzoateYield 93.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 mL round bottom flask equipped with efficient magnetic stirring was charged with o-phenylphenol (17.0 g, 0.1 mol), toluene (100 mL) and triethylamine (11.1 g, 0.11mol, 10% excess). Benzoyl chloride (14.7 g, 0.105 mol, 5% excess) was added portionwise over 15 minutes while using an ice bath to help maintain the temperature below 30° C. The initially clear reaction mixture became a white slurry during the acid chloride addition. After stirring at room temperature for an additional 2.5 hours, the slurry was filtered and the clear organic layer was stripped on a rotary evaporator at 60° C./P=3.4 kPa. The light yellow oil crystallized upon cooling. The crude product was recrystallized from a mixture of hexane (100 mL)/toluene (20 mL) yielding 25.7 g (93.8%) white crystals. The structure was confined using 13C and 1H NMR, IR and GC/MS.

Workup

  1. customA 250 mL round bottom flask equipped with efficient
  2. temperatureto help maintain the temperature below 30° C
  3. stirringAfter stirring at room temperature for an additional 2.5 hours
  4. filtrationthe slurry was filtered
  5. customthe clear organic layer was stripped on a rotary evaporator at 60° C./P=3.4 kPa
  6. customThe light yellow oil crystallized
  7. temperatureupon cooling
  8. customThe crude product was recrystallized from a mixture of hexane (100 mL)/toluene (20 mL)

Sources & evidence

ORD record
ord-48d7fde793b94b179dada805603db3c4
Source dataset
uspto-grants-2015_02
Patent number
US08961624B2

Reaction notes

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