Acetic Acid → (1,1'-Biphenyl)-2,3'-diol

HRID 324602

Reaction equation

HRID 324602 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.C[CH2:10][C:11](=[O:14])[CH2:12][CH3:13].OS(O)(=O)=O.[C:20](O)(=O)C>>[CH:3]1[CH:2]=[C:1]([C:8]2[CH:20]=[CH:13][CH:12]=[C:11]([OH:14])[CH:10]=2)[C:6]([OH:7])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 335O-CresolHCID 1118Sulfuric AcidHCID 7288Ethyl ketone

Product 1

HCID 33665(1,1'-Biphenyl)-2,3'-diol

Procedure

To a solution of o-cresol (5 g, 46.3 mmol) and 3-pentanone (2 g, 23.2 mmol) in acetic acid (20 mL) was added conc H2SO4 (4 mL). The reaction mixture was stirred at ambient temperature for 3 days, poured over ice, and diluted with 1:5 ethyl acetate/hexanes. The organic fraction was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 5% ethyl acetate in hexanes) afforded 2.2 g of diphenol 6. 1HNMR (CDCl3) δ: 6.90 (d, J=2 Hz, 2 H, Ar—H), 6.95 (dd, J=2 Hz, J=8.6 Hz, 2 H, Ar—H), 6.64 (d, J=8.6 Hz, 2 H, Ar—H), 2.21 (s, 6 H, Ar—CH3), 2.0 (q, J=7.3 Hz, 4 H, CH2CH3), 0.60 (t, J=7.3 Hz, 4 H, CH2CH3).

Workup

  1. additionpoured over ice
  2. customThe organic fraction was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01999415c2004771aa7852c72a5058de
Source dataset
uspto-grants-2001_04
Patent number
US06218430B1

Linked notes

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