2,6-Dimethoxybiphenyl → [1,1'-Biphenyl]-2,6-diol

HRID 1676874Notes

Reaction equation

HRID 1676874 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[NH+]1C=CC=CC=1>O>[C:4]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([OH:2])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:9]

Participants

4

Reactant 2

HCID 9142572,6-DimethoxybiphenylHCID 21584435Pyridinium hydrochloride

Product 1

HCID 15007745[1,1'-Biphenyl]-2,6-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Dimethoxybiphenyl (5.00 g) and 15 g of pyridinium hydrochloride were placed in the round-bottom flask and immersed in the oil bath (210° C., 1.5 hours). Then the reaction was cooled down to room temperature, diluted with 200 ml of water and extracted with ethyl acetate (4×50 ml). Organic fractions were combined, dried over sodium sulfate and evaporated. The residue was subjected to column chromatography on silica gel (eluent hexane/ethyl acetate 1/1 mixture), providing 3.3 of biphenyl-2,6-diol as yellow solid.

Workup

  1. customimmersed in the oil bath (210° C., 1.5 hours)
  2. extractionextracted with ethyl acetate (4×50 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-25b0a562b5e846feb9b0f914fd05b144
Source dataset
uspto-grants-2011_08
Patent number
US08007927B2

Reaction notes

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