GB600865A - Improvements in or relating to a process of preparing butyrolactones - Google Patents
Improvements in or relating to a process of preparing butyrolactonesInfo
- Publication number
- GB600865A GB600865A GB2677945A GB2677945A GB600865A GB 600865 A GB600865 A GB 600865A GB 2677945 A GB2677945 A GB 2677945A GB 2677945 A GB2677945 A GB 2677945A GB 600865 A GB600865 A GB 600865A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- acid
- acetate
- butyrolactone
- ethyl
- 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
Links
- YEJRWHAVMIAJKC-UHFFFAOYSA-N γ-lactone 4-hydroxy-butyric acid Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 4
- 229960000583 Acetic Acid Drugs 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- OBLYWUBMZGHQDN-UHFFFAOYSA-M 2,2-dichlorobutanoate Chemical compound CCC(Cl)(Cl)C([O-])=O OBLYWUBMZGHQDN-UHFFFAOYSA-M 0.000 abstract 2
- 229910000497 Amalgam Inorganic materials 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 235000011056 potassium acetate Nutrition 0.000 abstract 2
- 235000019260 propionic acid Nutrition 0.000 abstract 2
- GSCLMSFRWBPUSK-UHFFFAOYSA-N β-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 abstract 2
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 abstract 1
- MQJKLMCFKPSRHH-MSFXPVEOSA-N C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C(O)C[C@H](CC)[C@@]1(C)CC2 Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C(O)C[C@H](CC)[C@@]1(C)CC2 MQJKLMCFKPSRHH-MSFXPVEOSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- XIXADJRWDQXREU-UHFFFAOYSA-M Lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 abstract 1
- 229940071257 Lithium acetate Drugs 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal acetate Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001649 bromium compounds Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- PSBAZVJEUNOIDU-UHFFFAOYSA-L potassium;sodium;diacetate Chemical compound [Na+].[K+].CC([O-])=O.CC([O-])=O PSBAZVJEUNOIDU-UHFFFAOYSA-L 0.000 abstract 1
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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
a - Halo - b - substituted-butyrolactones of the general formula: <FORM:0600865/IV(b)/1> in which R is a monovalent acylic or carbocyclic radical, which is linked through a saturated carbon atom of the radical to the b carbon atom of butyrolactone nucleus, and X is chlorine, bromine or iodine are obtained by treating an ester of the acid of the formula: R-C.(OH).(CH3)-CH.X-COOH with a solution of hydrogen bromide in a liquid saturated aliphatic acid, e.g. acetic or propionic acid. Preferably the ester is an alkyl ester. The a -halo-b -R-butyrolactone may be dehydrogenated by treating with an anhydrous alkali metal acetate, such as potassium acetate, sodium acetate or lithium acetate in a liquid saturated aliphatic acid such as acetic acid, propionic acid or butyric acid to produce a b -R-D a b -butyrolactone. In examples: (1) ethyl - a chloro - b - hydroxy - b - cyclohexylbutyrate (obtained by condensing ethyl dichloroacetate with methyl cyclohexyl ketone in the presence of magnesium amalgam) in glacial acetic acid is saturated with hydrogen bromide and refluxed to produce a -chloro-b -cyclohexylbutyrolactone. This product heated with anhydrous potassium acetate in glacial acetic acid yields b -cyclohexyl-D a b -butyrolactone; (2) as in (1) except that the bromo derivative is produced; (3) ethyl a -chloro-b -b -hydroxy-b -etiocholanylbutyrate is treated as in (1) to produce a -chloro-b -etiocholanyl butyrolactone and 3, 14-bisdesoxythevetigin; (4) ethyl - 2 - chloro - b - hydroxy - b - 3(b )-acetoxy etiocholanylbutyrate (obtained by condensing pregnanol - 3(b ) - one - 20 -acetate with ethyl dichloroacetate in the presence of magnesium amalgam) is treated as in (1) to produce a - chloro - b - 3(b ) - acetoxy etiocholanylbutyrolactone and 14 - desoxythevetigenin acetate. The latter compound on hydrolysis with hydrochloric acid forms 14-desoxythevetigenin.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB600865A true GB600865A (en) | 1948-04-21 |
Family
ID=1740225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2677945A Expired GB600865A (en) | 1945-10-12 | Improvements in or relating to a process of preparing butyrolactones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB600865A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1048662A1 (en) * | 1997-12-26 | 2000-11-02 | Daiso Co., Ltd. | Novel process for producing 3-hydroxy-gamma-butyrolactone derivatives |
-
1945
- 1945-10-12 GB GB2677945A patent/GB600865A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1048662A1 (en) * | 1997-12-26 | 2000-11-02 | Daiso Co., Ltd. | Novel process for producing 3-hydroxy-gamma-butyrolactone derivatives |
| EP1048662A4 (en) * | 1997-12-26 | 2002-01-16 | Daiso Co Ltd | Novel process for producing 3-hydroxy-gamma-butyrolactone derivatives |
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