JPS55160740A - Preparation of cyclopentenolone - Google Patents

Preparation of cyclopentenolone

Info

Publication number
JPS55160740A
JPS55160740A JP6849579A JP6849579A JPS55160740A JP S55160740 A JPS55160740 A JP S55160740A JP 6849579 A JP6849579 A JP 6849579A JP 6849579 A JP6849579 A JP 6849579A JP S55160740 A JPS55160740 A JP S55160740A
Authority
JP
Japan
Prior art keywords
formula
compound
cyclopentenone
grignard reagent
reacted
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.)
Granted
Application number
JP6849579A
Other languages
Japanese (ja)
Other versions
JPS6126894B2 (en
Inventor
Kenji Saito
Hiroshi Yamachika
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co 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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP6849579A priority Critical patent/JPS55160740A/en
Priority to US06/151,603 priority patent/US4371711A/en
Priority to EP80102834A priority patent/EP0022162B1/en
Priority to DE8080102834T priority patent/DE3062712D1/en
Publication of JPS55160740A publication Critical patent/JPS55160740A/en
Priority to US06/420,082 priority patent/US4465862A/en
Publication of JPS6126894B2 publication Critical patent/JPS6126894B2/ja
Granted legal-status Critical Current

Links

Abstract

PURPOSE: To obtain the title compound useful as an intermediate material for agricultural chemicals, in high yield in four stages, by the reaction of a furylcarbinol prepared from furfural and a Grignard reagent, via a cyclopentenone, a cyclopentenedione and a cyclopentenone successively.
CONSTITUTION: A furylcarbinol compound of formula I produced from furfural and a Grignard reagent of formula R1MgX [R1 is (cyclo)alkyl, alkenyl, alkynyl, thienyl, phenyl, p-methylbenzyl or benzyl; X is Cl, Br or I] is reacted in a water-organic solvent, in the presence of an acid, to give a cyclopentenone compound of formula II, which is oxidized to form a cyclopentenedione compound of formula III, and then reacted with a Grignard reagent of formula R2MgX (R2 is alkyl, alkenyl, or alkynyl), to prepare a cyclopentenone compound of formula IV. The resulting compound is further reacted in the presence of a base, to give the object compound of formula V.
COPYRIGHT: (C)1980,JPO&Japio
JP6849579A 1979-05-30 1979-05-31 Preparation of cyclopentenolone Granted JPS55160740A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP6849579A JPS55160740A (en) 1979-05-31 1979-05-31 Preparation of cyclopentenolone
US06/151,603 US4371711A (en) 1979-05-30 1980-05-20 Process for producing 4-hydroxycyclopentenones
EP80102834A EP0022162B1 (en) 1979-05-30 1980-05-21 Process for producing disubstituted 4-hydroxycyclopentenones; monosubstituted cyclopentendiones and 4-hydroxycyclopentenones
DE8080102834T DE3062712D1 (en) 1979-05-30 1980-05-21 Process for producing disubstituted 4-hydroxycyclopentenones; monosubstituted cyclopentendiones and 4-hydroxycyclopentenones
US06/420,082 US4465862A (en) 1979-05-30 1982-09-20 Cyclopentendione and cyclopentenone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6849579A JPS55160740A (en) 1979-05-31 1979-05-31 Preparation of cyclopentenolone

Publications (2)

Publication Number Publication Date
JPS55160740A true JPS55160740A (en) 1980-12-13
JPS6126894B2 JPS6126894B2 (en) 1986-06-23

Family

ID=13375325

Family Applications (1)

Application Number Title Priority Date Filing Date
JP6849579A Granted JPS55160740A (en) 1979-05-30 1979-05-31 Preparation of cyclopentenolone

Country Status (1)

Country Link
JP (1) JPS55160740A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58111690A (en) * 1981-12-25 1983-07-02 Sumitomo Chem Co Ltd L(-)-2-allyl-3-hydroxy-3-methyl-4-cyclopentenone and its preparation
CN111253231A (en) * 2020-02-03 2020-06-09 厦门大学 Preparation method of 4-cyclopentene-1, 3-dione

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58111690A (en) * 1981-12-25 1983-07-02 Sumitomo Chem Co Ltd L(-)-2-allyl-3-hydroxy-3-methyl-4-cyclopentenone and its preparation
JPH0428358B2 (en) * 1981-12-25 1992-05-14 Sumitomo Chemical Co
CN111253231A (en) * 2020-02-03 2020-06-09 厦门大学 Preparation method of 4-cyclopentene-1, 3-dione
CN111253231B (en) * 2020-02-03 2021-08-03 厦门大学 Preparation method of 4-cyclopentene-1, 3-dione

Also Published As

Publication number Publication date
JPS6126894B2 (en) 1986-06-23

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