US3880937A - Process for preparing 3-alkyl-5-t-butylphenols - Google Patents

Process for preparing 3-alkyl-5-t-butylphenols Download PDF

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Publication number
US3880937A
US3880937A US133754A US13375471A US3880937A US 3880937 A US3880937 A US 3880937A US 133754 A US133754 A US 133754A US 13375471 A US13375471 A US 13375471A US 3880937 A US3880937 A US 3880937A
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US
United States
Prior art keywords
alkyl
butylphenols
butylphenol
aluminum chloride
preparing
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Expired - Lifetime
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US133754A
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English (en)
Inventor
Katsuzo Kamoshita
Shinji Nakai
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the present invention relates to a process for preparing 3-alkyl-5-t-butylphenols. More particularly, it is concerned with a process for preparing 3-alkyl-5-tbutylphenols in high yields which comprises contacting 3-alkyl-6-t-butylphenols with aluminum chloride under a mild condition to rearrange the t-butyl group at the 6-position to the 5-position, the alkyl being an alkyl having 1 to 3 carbon atoms.
  • m-alkylphenols can be produced by heating the corresponding oor palkylphenols above 125C in the presence of a strong acid and a natural or synthetic alumina-silicate to rearrange the alkyl group at the oor p-position to the mposition [U.S. Pat. No. 3,014,079].
  • this procedure is applied to 3-alkyl-6-t-butylphenols, however, the elimination of the t-butyl group preferentially takes place rather than the rearrangement of the t-butyl group so that 3-alkyl-5-t-butylphenols are obtained only in trace.
  • the application to o-t-butylphenol gives p-t-butylphenol in a high yield with no material production of the corresponding m-isomer.
  • the application to 2-t-butyl-4- methylphenol results in the elimination of the t-butyl group to give p-cresol.
  • the rearrangement of the tbutyl group to the m-position does not take place.
  • the present invention is based on the said finding.
  • 3-alkyl-6-tbutylphenols are treated with aluminum chloride at a temperature below 70C, preferably of to 30C while stirring for 2 to 4 hours at atmospheric pressure whereby the rearrangement of the t-butyl group at the 6-position to the -position takes place to give 3-alkyl- S-t-butylphenols.
  • the amount of aluminum chloride to be used may be 0.25 to 2 mol, preferably 1 mol, per mol of the starting phenol.
  • 3-alkyl-5-t-butylphenols are utilizable as intermediates in the production of various per se useful substances.
  • the reaction with methyl isocyanate affords 3-alkyl-5-t-butylphenol N- methylcarbamates, which are insecticides exerting a strong controlling activity against various harmful insects without any toxicity to mammals.
  • the oily product before fractional distillation is con- 8 firmed to have the following composition by gas chromatography:
  • a process for preparing a 3-alkyl-5-t-butylphenol which comprises contacting a 3-alkyl-6-t-butylphenol with aluminum chloride at a temperature between about 0 and 30C to rearrange the t-butyl group at the 6-position to the 5-position, the alkyl group having 1 to 3 carbon atoms.
US133754A 1970-04-15 1971-04-13 Process for preparing 3-alkyl-5-t-butylphenols Expired - Lifetime US3880937A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP45032558A JPS49822B1 (de) 1970-04-15 1970-04-15

Publications (1)

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US3880937A true US3880937A (en) 1975-04-29

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US133754A Expired - Lifetime US3880937A (en) 1970-04-15 1971-04-13 Process for preparing 3-alkyl-5-t-butylphenols

Country Status (7)

Country Link
US (1) US3880937A (de)
JP (1) JPS49822B1 (de)
CH (1) CH548351A (de)
DE (1) DE2117435C3 (de)
FR (1) FR2089654A5 (de)
GB (1) GB1296179A (de)
NL (1) NL7104828A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4334101A (en) * 1977-02-01 1982-06-08 Snamprogetti S.P.A. Method for preparing metal-carbonyl clusters immobilized in zeolite and their use as heterogeneous catalysts

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2558522C3 (de) * 1975-12-24 1986-07-31 Bayer Ag, 5090 Leverkusen Verfahren zur kontinuierlichen Herstellung von Di-tertiär-butylkresolen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2107060A (en) * 1935-12-06 1938-02-01 Sharples Solvents Corp Method of preparing phenolic compounds
US3014079A (en) * 1958-02-21 1961-12-19 Pennsalt Chemicals Corp Process for preparing metaalkylphenols

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2107060A (en) * 1935-12-06 1938-02-01 Sharples Solvents Corp Method of preparing phenolic compounds
US3014079A (en) * 1958-02-21 1961-12-19 Pennsalt Chemicals Corp Process for preparing metaalkylphenols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4334101A (en) * 1977-02-01 1982-06-08 Snamprogetti S.P.A. Method for preparing metal-carbonyl clusters immobilized in zeolite and their use as heterogeneous catalysts

Also Published As

Publication number Publication date
GB1296179A (de) 1972-11-15
NL7104828A (de) 1971-10-19
DE2117435C3 (de) 1974-12-12
DE2117435A1 (de) 1971-11-04
JPS49822B1 (de) 1974-01-10
FR2089654A5 (de) 1972-01-07
CH548351A (de) 1974-04-30
DE2117435B2 (de) 1974-05-09

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