Trifluoromethanesulfonic acid → 4,4'-Dihydroxybiphenyl

HRID 1154092Notes

Reaction equation

HRID 1154092 reaction equation
CC([C:5]1[C:25](=[O:26])[C:24](C(C)(C)C)=[CH:23][C:7](=[C:8]2[CH:14]=[C:13](C(C)(C)C)[C:11](=[O:12])[C:10](C(C)(C)C)=[CH:9]2)[CH:6]=1)(C)C.FC(F)(F)S(O)(=O)=O>C(C1C=CC=CC=1)C>[C:11]1([OH:12])[CH:10]=[CH:9][C:8]([C:7]2[CH:23]=[CH:24][C:25]([OH:26])=[CH:5][CH:6]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 2252833,3',5,5'-Tetra-tert-butyl-4,4'-dibenzoquinone

Product 1

HCID 71124,4'-DihydroxybiphenylYield 87.7%

Reagents, catalysts & solvents 1

HCID 7500EthylbenzeneSolvent

Procedure

10 g (24.5 mmole) of 3,3',5,5',-tetra-tert-butyl-diphenoquinone in 40 ml ethylbenzene was hydrogenated as in Example 9. The filtrate was transferred to a popbottle containing 1.5 g (10 mmol) trifluoromethane sulfonic acid and a magnetic stirring bar. The reaction mixture was kept at 120° C. for 45 minutes. 4 g of 4,4'-biphenol was obtained as white material after recrystallization from acetone (88% yield). The filtrate contained 13.8 g (85.2 mmol) of p- and m-tert-butyl-ethyl-benzene (86.9% yield).

Sources & evidence

ORD record
ord-129049b91141497fa8f8569e8d51d36e
Source dataset
uspto-grants-1984_12
Patent number
US04487978

Reaction notes

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