CA1057762A - Organic di-esters of 2,5 dihydroxy-1,4-dioxanes and process for their preparation - Google Patents
Organic di-esters of 2,5 dihydroxy-1,4-dioxanes and process for their preparationInfo
- Publication number
- CA1057762A CA1057762A CA227,118A CA227118A CA1057762A CA 1057762 A CA1057762 A CA 1057762A CA 227118 A CA227118 A CA 227118A CA 1057762 A CA1057762 A CA 1057762A
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- alkaline
- rcoo
- salt
- formula
- 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
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- ATFVTAOSZBVGHC-UHFFFAOYSA-N Glycolaldehyde dimer Chemical class OC1COC(O)CO1 ATFVTAOSZBVGHC-UHFFFAOYSA-N 0.000 title 1
- 150000005690 diesters Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- UHZHZLIEBDGGME-UHFFFAOYSA-N 2,5-dichloro-1,4-dioxane Chemical compound ClC1COC(Cl)CO1 UHZHZLIEBDGGME-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NTODSQZMFWVBFF-UHFFFAOYSA-N (5-acetyloxy-1,4-dioxan-2-yl) acetate Chemical compound CC(=O)OC1COC(OC(C)=O)CO1 NTODSQZMFWVBFF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2287274A IT1012481B (it) | 1974-05-17 | 1974-05-17 | Diesteri organici dei 2.5 diidros si 1.4 diossani e processo per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057762A true CA1057762A (en) | 1979-07-03 |
Family
ID=11201393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,118A Expired CA1057762A (en) | 1974-05-17 | 1975-05-16 | Organic di-esters of 2,5 dihydroxy-1,4-dioxanes and process for their preparation |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS51110578A (enExample) |
| BE (1) | BE829047A (enExample) |
| CA (1) | CA1057762A (enExample) |
| CH (1) | CH605904A5 (enExample) |
| DE (1) | DE2521703A1 (enExample) |
| FR (1) | FR2271224B1 (enExample) |
| GB (1) | GB1503794A (enExample) |
| IT (1) | IT1012481B (enExample) |
| LU (1) | LU72492A1 (enExample) |
| NL (1) | NL7505831A (enExample) |
-
1974
- 1974-05-17 IT IT2287274A patent/IT1012481B/it active
-
1975
- 1975-05-14 CH CH621575A patent/CH605904A5/xx not_active IP Right Cessation
- 1975-05-14 BE BE156325A patent/BE829047A/xx not_active IP Right Cessation
- 1975-05-15 DE DE19752521703 patent/DE2521703A1/de active Pending
- 1975-05-15 GB GB2073675A patent/GB1503794A/en not_active Expired
- 1975-05-16 CA CA227,118A patent/CA1057762A/en not_active Expired
- 1975-05-16 NL NL7505831A patent/NL7505831A/xx unknown
- 1975-05-16 FR FR7515525A patent/FR2271224B1/fr not_active Expired
- 1975-05-16 JP JP5749375A patent/JPS51110578A/ja active Granted
- 1975-05-16 LU LU72492A patent/LU72492A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2271224B1 (enExample) | 1978-09-22 |
| CH605904A5 (enExample) | 1978-10-13 |
| JPS5337869B2 (enExample) | 1978-10-12 |
| IT1012481B (it) | 1977-03-10 |
| FR2271224A1 (enExample) | 1975-12-12 |
| BE829047A (fr) | 1975-09-01 |
| GB1503794A (en) | 1978-03-15 |
| LU72492A1 (enExample) | 1975-08-28 |
| JPS51110578A (en) | 1976-09-30 |
| NL7505831A (nl) | 1975-11-19 |
| DE2521703A1 (de) | 1975-11-20 |
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