JPS55160740A - Preparation of cyclopentenolone - Google Patents
Preparation of cyclopentenoloneInfo
- 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
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
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)
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 |
-
1979
- 1979-05-31 JP JP6849579A patent/JPS55160740A/en active Granted
Cited By (4)
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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