Methanesulfonic Acid → 4,4'-Dihydroxybiphenyl

HRID 2120343Notes

Reaction equation

HRID 2120343 reaction equation
C([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15](C(C)(C)C)[C:14]([OH:21])=[C:13](C(C)(C)C)[CH:12]=2)[CH:8]=[C:7](C(C)(C)C)[C:6]=1[OH:30])(C)(C)C.CS(O)(=O)=O.CCCCCCCCC(C)C>C1(C)C=CC=CC=1>[C:14]1([OH:21])[CH:13]=[CH:12][C:11]([C:9]2[CH:10]=[CH:5][C:6]([OH:30])=[CH:7][CH:8]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 234152-MethyldecaneHCID 671854,4'-Bis(2,6-di-tert-butylphenol)

Product 1

HCID 71124,4'-DihydroxybiphenylYield 99.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three-necked flask 50 grams of 2,2′,6,6′-tetra-t-butyl-4,4′-biphenol (I) and 0.25 gm of methanesulfonic acid were mixed with a mixture of 80 ml Isopar-G (hydrocarbons C10-C11) and 20 ml of toluene. After 2 hours at 150° C., 26 grams of isobutylene is collected in a dry ice trap and the reaction cooled to room temperature and was filtered. The biphenol was dried at 130° C., giving 22.5 gram of 4,4′-biphenol (99% yield) with purity >99% were collected.

Workup

  1. custom26 grams of isobutylene is collected in a dry ice trap
  2. filtrationwas filtered
  3. dry with materialThe biphenol was dried at 130° C.

Sources & evidence

ORD record
ord-16523fd3bbe446c99995358c9c0ea2b7
Source dataset
uspto-grants-2004_02
Patent number
US06689921B2

Reaction notes

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