GB1179250A - Benzofuran Derivatives - Google Patents

Benzofuran Derivatives

Info

Publication number
GB1179250A
GB1179250A GB5496366A GB5496366A GB1179250A GB 1179250 A GB1179250 A GB 1179250A GB 5496366 A GB5496366 A GB 5496366A GB 5496366 A GB5496366 A GB 5496366A GB 1179250 A GB1179250 A GB 1179250A
Authority
GB
United Kingdom
Prior art keywords
formula
methoxy
compounds
methallyloxy
reacting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB5496366A
Inventor
John Gillon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fisons Pest Control Ltd
Original Assignee
Fisons Pest Control Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fisons Pest Control Ltd filed Critical Fisons Pest Control Ltd
Priority to GB5496366A priority Critical patent/GB1179250A/en
Priority to DE19671643352 priority patent/DE1643352A1/en
Priority to BE703726D priority patent/BE703726A/xx
Priority to CH1271567A priority patent/CH475975A/en
Priority to NL6712601A priority patent/NL6712601A/xx
Priority to FR1548441D priority patent/FR1548441A/fr
Publication of GB1179250A publication Critical patent/GB1179250A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

1,179,250. Benzofuran derivatives. FISONS PEST CONTROL Ltd. 24 Aug., 1967 [16 Sept., 1966; 8 Dec., 1966], Nos. 41466/66 and 54963/66. Heading C2C. Novel 2,3-dihydro-2-methyl-7-alkoxy -benzofurans of Formula (I) wherein R<SP>1</SP> is hydrogen or methyl, R<SP>2</SP> and R<SP>3</SP> (which are the same or different) are hydrogen or alkyl (C 1 -C 5 ), R<SP>4</SP> is alkyl (C 1 -C 5 ) and R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP> (which are the same or different) are hydrogen, alkyl (C 1 -C 5 ), or halogen are prepared either by reacting 1 - alkoxy - 2 - alkenyloxybenzenes of the Formula (II) with one or more Claisen rearrangement catalysts (e.g. anhydrous magnesium chloride) at elevated temperatures to effect a Claisen rearrangement and cyclization in a single step or by converting compounds of Formula (II) to those of Formula (III) by heating with a tertiary base and then reacting compounds of Formula (III) with a cyclization agent (e.g. formic acid, phosphoric acid, or a hydrobromic acid/acetic acid mixture). Compounds of Formula (I) may be converted into benzofuranols by reacting with pyridine hydrochloride or pyridine base hydrochloride at an elevated temperature; the benzofuranols in turn may be converted to carbamates by forming the chloroformates followed by reaction with an amine. As starting materials, compounds of Formula (II), viz. 1 - methoxy - 2 - methallyloxybenzene, 1 - methoxy - 2 - methallyloxy - 4 - methylbenzene, 1 - chloro - 4 - methallyloxy - 3 - methoxy - benzene and 4-methallyloxy-3-methoxy-toluene are prepared by reacting the correspondingly substituted methoxy phenols with methallyl chloride. Compounds of Formula (III) isolated are 2- methallyl - 6 - methoxyphenol, 2 - methallyl - 3 - methyl - 6 - methoxyphenol, 4 - chloro - 6 - methallyl - 2 - methoxyphenol and 4 - methallyloxy - 3 - methoxytoluene.
GB5496366A 1966-09-16 1966-09-16 Benzofuran Derivatives Expired GB1179250A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB5496366A GB1179250A (en) 1966-09-16 1966-09-16 Benzofuran Derivatives
DE19671643352 DE1643352A1 (en) 1966-09-16 1967-08-29 Process for the preparation of 2,3-dihydro-2-methyl-7-alkoxy-benzofurans
BE703726D BE703726A (en) 1966-09-16 1967-09-11
CH1271567A CH475975A (en) 1966-09-16 1967-09-12 Process for the preparation of dihydro alkoxy benzofurans
NL6712601A NL6712601A (en) 1966-09-16 1967-09-14
FR1548441D FR1548441A (en) 1966-09-16 1967-09-14

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4146666 1966-09-16
GB5496366A GB1179250A (en) 1966-09-16 1966-09-16 Benzofuran Derivatives

Publications (1)

Publication Number Publication Date
GB1179250A true GB1179250A (en) 1970-01-28

Family

ID=26264683

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5496366A Expired GB1179250A (en) 1966-09-16 1966-09-16 Benzofuran Derivatives

Country Status (6)

Country Link
BE (1) BE703726A (en)
CH (1) CH475975A (en)
DE (1) DE1643352A1 (en)
FR (1) FR1548441A (en)
GB (1) GB1179250A (en)
NL (1) NL6712601A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4256647A (en) 1978-11-30 1981-03-17 Philagro Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofurane

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2470768A1 (en) * 1979-12-07 1981-06-12 Rhone Poulenc Agrochimie PROCESS FOR THE PREPARATION OF BENZOFURAN DERIVATIVES

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4256647A (en) 1978-11-30 1981-03-17 Philagro Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofurane

Also Published As

Publication number Publication date
FR1548441A (en) 1968-12-06
CH475975A (en) 1969-07-31
BE703726A (en) 1968-03-11
NL6712601A (en) 1968-03-18
DE1643352A1 (en) 1971-02-25

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