tert-Butanol → [1,1'-Biphenyl]-4-ol, 3-(1,1-dimethylethyl)-

HRID 1062524Notes

Reaction equation

HRID 1062524 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](O)([CH3:17])([CH3:16])[CH3:15].CCCCCC>C1(C)C=CC=CC=1>[C:14]([C:11]1[CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]=1[OH:13])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 71034-HydroxybiphenylHCID 8058Hexane

Product 1

HCID 162519[1,1'-Biphenyl]-4-ol, 3-(1,1-dimethylethyl)-Yield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a 300 ml reactor thoroughly dried and purged with nitrogen, 34.04 g (200.0 mmol) of 4-phenylphenol, 3.40 g of Umberist-15E (trade name, available from Organo Co.) and 150 ml of toluene were introduced. To the reactor, a solution containing 48.20 g (200.0 mmol) of t-butyl alcohol diluted with 10 ml of a toluene was dropwise added at 105° C., followed by stirring for 16 hours. After the system was cooled to room temperature, the solution was introduced into 500 ml of hexane and filtered with washing with hexane. After concentration, the resulting liquid was purified by silica gel column chromatography to obtain 31.15 g (yield: 69%) of 2-t-butyl-4-phenylphenol.

Workup

  1. customInto a 300 ml reactor thoroughly dried
  2. additionwere introduced
  3. additionwas dropwise added at 105° C.
  4. filtrationfiltered
  5. washwith washing with hexane
  6. concentrationAfter concentration
  7. customthe resulting liquid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18e6adcb686c446cb2dcda0aa7674e4a
Source dataset
uspto-grants-2005_11
Patent number
US06962890B2

Reaction notes

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