78-09-1

Basic information

• Product Name: Tetraethyl orthocarbonate
• Synonyms: ORTHOCARBONIC ACID TETRAETHYL ESTER;TETRAETHOXYMETHANE;TETRAETHYL ORTHOCARBONATE;1-(Triethoxymethoxy)ethane;1,1’,1’’,1’’’-[methanetetrayltetrakis(oxy)]tetrakis-ethan;Tetraehtylorthocarbonate;Tetraethyl-2-carbonate;Tetraethyl orthocarbonate, 98+%
• CAS NO: 78-09-1
• Molecular Formula: C₉H₂₀O₄
• Molecular Weight: 192.25
• EINECS: 201-082-2
• Product Categories: Acetals/Ketals/Ortho Esters;Organic Building Blocks;Oxygen Compounds
• Mol File: 78-09-1.mol

Chemical Properties

• Melting Point: 222 °C
• Boiling Point: 159 °C(lit.)
• Flash Point: 127 °F
• Appearance: clear colorless liquid
• Density: 0.919 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.24mmHg at 25°C
• Refractive Index: n20/D 1.392(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: Insoluble
• Sensitive: Moisture Sensitive
• BRN: 1747401
• CAS DataBase Reference: Tetraethyl orthocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraethyl orthocarbonate(78-09-1)
• EPA Substance Registry System: Tetraethyl orthocarbonate(78-09-1)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 37/39-26-16-36-24/25
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• F: 21
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 78-09-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tetraethyl orthocarbonate is used as a synthetic intermediate for the production of chemokine receptor-5 inhibitors against HIV-1, which play a crucial role in the development of antiretroviral drugs.
Used in Chemical Synthesis:
Tetraethyl orthocarbonate is used as a reagent in the synthesis of benzobisoxazoles, which are important building blocks in the development of pharmaceuticals, agrochemicals, and other organic compounds.
Used in Organic Semiconductor Industry:
Tetraethyl orthocarbonate is used as a precursor in the preparation of organic semiconductors, which are essential components in the fabrication of electronic devices such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs).
Used in Polymer Synthesis:
Tetraethyl orthocarbonate is used as a monomer in the synthesis of 2,7-dimethylene-1,4,6,9-tetraoxaspiro[4,4]nonane, a unique cyclic orthoester with potential applications in various industries.
Used in Environmental Applications:
Tetraethyl orthocarbonate is used as a building block in the synthesis of cross-linked poly(orthocarbonate)s, which are employed as organic solvent absorbents for the removal of pollutants from water and air.

Purification Methods

Likely impurities are hydrolysis products. Shake the orthocarbonate with brine (saturated NaCl, dilute with a little Et2O if amount of material is small) and dry (MgSO4). The organic layer is filtered off and evaporated, and the residue is distilled through a helices packed fractionating column with a total reflux partial take-off head. All distillations can be done at atmospheric pressure in an inert atmosphere (e.g. N2). [Roberts & McMahon Org Synth Coll Vol IV 457 1963, Connolly & Dyson J Chem Soc 828 1937, Tieckelmann & Post J Org Chem 13 266 1948, for review see Kantlehner et al. Justus Liebigs Ann Chem 507 207 1982, Beilstein 3 IV 6.]

InChI:InChI=1/C9H20O4/c1-5-10-9(11-6-2,12-7-3)13-8-4/h5-8H2,1-4H3

Synthetic route

ethanol (64-17-5) + chloropicrin (76-06-2) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With sodium ethanolate at 65 - 70℃; for 3h; Temperature; Large scale;	91%
With sodium Darst.;

ethyl 2,2,2-trichloroacetimidate (23213-96-9) + sodium methylate (124-41-4) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
In ethanol for 1h; Heating;	85%

sodium ethanolate (141-52-6) + trichloroacetonitrile (545-06-2) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
In ethanol for 3.5h; Heating / reflux;	83%
In ethanol Heating;

tetrachloromethane (56-23-5) + ethanol (64-17-5) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
at 80 - 95℃; for 5h; Temperature;	83%

ethanol (64-17-5) + triethoxyacetonitrile (68714-37-4) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With toluene-4-sulfonic acid Heating;	71%

triethoxyacetonitrile (68714-37-4) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1) + Triethylmethylorthocarbonat (81759-13-9) + Trimethylethylorthocarbonat (81759-14-0)

Conditions	Yield
In ethanol 1.) 5 min, 60 deg C, 2.) 30 min, to room temperature; Title compound not separated from byproducts;	A 70% B 58% C 2%

carbon disulfide (75-15-0) + ethanol (64-17-5) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With silver trifluoroacetate; triethylamine for 5h; Ambient temperature;	61%
Yield given. Multistep reaction;

triethoxyacetonitrile (68714-37-4) + N-butylamine (109-73-9) → orthocarbonic acid tetraethyl ester (78-09-1) + Diethyl(butylimido)carbonat (81759-28-6) + 1,3-Dibutyl-2-ethylisoharnstoff (81759-30-0)

Conditions	Yield
at 120℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;	A n/a B n/a C 59%
at 120℃; Heating; Yields of byproduct given;	A n/a B n/a C 59%

chloropicrin (76-06-2) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
In ethanol at 57 - 64℃; for 2h; Heating / reflux; Industry scale;	58.3%

triethoxyacetonitrile (68714-37-4) + sodium methylate (124-41-4) → orthocarbonic acid tetraethyl ester (78-09-1) + Triethylmethylorthocarbonat (81759-13-9) + Trimethylethylorthocarbonat (81759-14-0)

Conditions	Yield
In methanol at 60℃; Title compound not separated from byproducts;	A 8 % Chromat. B 58% C 2 % Chromat.

3,3-diethoxypentane (36749-09-4) → orthocarbonic acid tetraethyl ester (78-09-1) + 3-chloro-benzoic acid ethyl ester (1128-76-3) + Ethyl propionate (105-37-3) + Diethyl carbonate (105-58-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 15 - 30℃; for 0.5h; Further byproducts given;	A 18% B n/a C n/a D 50%

triethoxyacetonitrile (68714-37-4) + benzylamine (100-46-9) → orthocarbonic acid tetraethyl ester (78-09-1) + Diethyl(benzylimido)carbonat (6263-03-2) + 1,3-Dibenzyl-2-ethylisoharnstoff (81759-29-7)

Conditions	Yield
at 120℃;	A n/a B 45% C 14%
at 120℃; Heating;	A n/a B 45% C 14%

Triethyl orthopropionate (115-80-0) → orthocarbonic acid tetraethyl ester (78-09-1) + Diethyl carbonate (105-58-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 15 - 30℃; for 0.5h;	A 25% B 45%

sodium methylate (124-41-4) + trichloroacetonitrile (545-06-2) → orthocarbonic acid tetraethyl ester (78-09-1) + ethyl 2,2,2-trichloroacetimidate (23213-96-9) + triethoxyacetonitrile (68714-37-4) + Ethyl-triethoxyacetimidat (77388-04-6)

Conditions	Yield
In n-heptane at 94℃; for 2h;	A n/a B n/a C n/a D 5.5%

tetrachloromethane (56-23-5) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1) + orthoformic acid triethyl ester (122-51-0)

diethyl ether (60-29-7) + carbon tetrabromide (558-13-4) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1)

carbon tetrabromide (558-13-4) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With diethyl ether

trichloro-methanesulfenic acid ethyl ester (13029-05-5) + sodium ethanolate (141-52-6) → orthocarbonic acid tetraethyl ester (78-09-1)

diethyl ether (60-29-7) + ethanol (64-17-5) + sodium ethanolate (141-52-6) + chlorothio-trichloro-methane (594-42-3) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
bei Einw.;

sodium ethanolate (141-52-6) + chlorothio-trichloro-methane (594-42-3) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With diethyl ether

carbon disulfide (75-15-0) + tin(II) ethoxide (3173-69-1, 14791-99-2, 24126-00-9, 96473-13-1) → orthocarbonic acid tetraethyl ester (78-09-1)

ethanol (64-17-5) + N-(di-ethoxymethylene)-benzamide (15146-36-8) → orthocarbonic acid tetraethyl ester (78-09-1)

ethanol (64-17-5) + phenyl cyanate (1122-85-6) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With hydrogenchloride

ethanol (64-17-5) + dichlorodiphenoxymethane (4885-03-4) → orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
With pyridine Ambient temperature;

Acetyl cyanide (631-57-2) + N,N-Dimethyl-orthocarbamidsaeure-triethylester (73708-97-1) → N,N-dimethyl acetamide (127-19-5) + orthocarbonic acid tetraethyl ester (78-09-1) + triethoxyacetonitrile (68714-37-4) + 2,2-diethoxy-2-dimethylaminoacetonitrile (34644-32-1)

Conditions	Yield
In diethyl ether for 5h; Ambient temperature; Yield given;
In diethyl ether for 5h; Ambient temperature;

sodium methylate (124-41-4) + triethoxycarbenium tetrafluoroborate → tetramethoxymethane (1850-14-2) + orthocarbonic acid tetraethyl ester (78-09-1) + Triethylmethylorthocarbonat (81759-13-9) + Trimethylethylorthocarbonat (81759-14-0) + Diethyldimethylorthocarbonat

Conditions	Yield
In methanol for 12h; Product distribution; Ambient temperature; also with other sodium-alcoholates;

methyl 2-(trifluoroacetamido)acrylate (58137-35-2) + ketene diethyl acetal (2678-54-8) → C12H16F3NO5 + 1-trifluoroacetamido-2-ethoxy-4-oxocyclohex-2-ene-1-carboxylic acid methyl ester + ethyl 2-ethoxypropionate (7737-40-8) + orthocarbonic acid tetraethyl ester (78-09-1)

Conditions	Yield
In chloroform-d1 at 25℃; Product distribution; Michael-Dieckmann type reaction;

orthocarbonic acid tetraethyl ester (78-09-1) + aniline (62-53-3) → N,N',N''-triphenylguanidine (101-01-9)

Conditions	Yield
at 160 - 170℃; for 10h;	98%
at 120℃; for 3h; Product distribution; other times and temperatures;	21%
at 160℃;

4,5-dicyano-1H-imidazole (1122-28-7) + orthocarbonic acid tetraethyl ester (78-09-1) → 1-ethyl-4,5-dicyanoimidazole (133123-67-8)

Conditions	Yield
1) 0.5 h, 100 deg C 2) 2 h, 150 deg C;	96%

orthocarbonic acid tetraethyl ester (78-09-1) + 2-nitro-5-(trifluoromethyl)aniline (402-14-2) → C10H9F3N2O (1060705-50-1)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	96%

orthocarbonic acid tetraethyl ester (78-09-1) + 1,2-diamino-benzene (95-54-5) → 2-ethoxy-1H-benzo[d]imidazole (22219-23-4)

Conditions	Yield
Stage #1: orthocarbonic acid tetraethyl ester; 1,2-diamino-benzene With acetic acid at 70℃; for 2h; Stage #2: With potassium hydroxide In water at 20℃; for 1h;	94%
Stage #1: orthocarbonic acid tetraethyl ester; 1,2-diamino-benzene With acetic acid at 70℃; for 3h; Large scale; Stage #2: With potassium hydroxide for 1h; Large scale;	94.2%
In neat (no solvent) at 70℃; for 2h;	93%

orthocarbonic acid tetraethyl ester (78-09-1) + 4,5-dimethyl-2-nitrobenzenamine (6972-71-0) → C11H14N2O

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	94%

orthocarbonic acid tetraethyl ester (78-09-1) + 5-fluoro-2-nitroaniline (2369-11-1) → C9H9FN2O (1060705-58-9)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	94%

orthocarbonic acid tetraethyl ester (78-09-1) + 2-(((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-aminobenzoic acid-1-(((cyclohexyloxy)carbonyl)oxy)ethyl ester (1236156-65-2) → candesartan cilexetil (145040-37-5)

Conditions	Yield
With acetic acid In ethyl acetate at 30℃; Temperature;	93.9%
With acetic acid In toluene at 60℃; for 2h;	81%

orthocarbonic acid tetraethyl ester (78-09-1) + tert-butyl 3,4-diaminopyrrolidine-1-carboxylate hydrochloride → tert-butyl 2-ethoxy-3a,4,6,6a-tetrahydropyrrolo[3,4-d]imidazole-5(1H)-carboxylate

Conditions	Yield
at 20℃; for 17h;	93.4%

orthocarbonic acid tetraethyl ester (78-09-1) + trimethylsilylacetylene (1066-54-2) → trimethyl(3,3,3-triethoxyprop-1-yn-1-yl)silane (91022-26-3)

Conditions	Yield
Stage #1: trimethylsilylacetylene With magnesium; isopropyl bromide In diethyl ether at 10℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: orthocarbonic acid tetraethyl ester In diethyl ether at 20℃; for 1h; Inert atmosphere;	93%
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In diethyl ether at 20℃; Reflux; Stage #2: orthocarbonic acid tetraethyl ester In diethyl ether at 20℃; Reflux;	77%
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In diethyl ether at 20℃; Inert atmosphere; Heating; Stage #2: orthocarbonic acid tetraethyl ester In diethyl ether at 20℃; Inert atmosphere; Reflux;	70%

orthocarbonic acid tetraethyl ester (78-09-1) + 2-Amino-3-nitrobenzoic acid,ethyl ester (61063-11-4) → ethyl 2-ethoxy-3H-benzimidazole-4-carboxylate (577957-02-9)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	93%

orthocarbonic acid tetraethyl ester (78-09-1) + 4-methyl-2-nitroaniline (89-62-3) → C10H12N2O (71468-10-5)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	93%

orthocarbonic acid tetraethyl ester (78-09-1) + C30H32N6O5*C2H2O4 → candesartan cilexetil (145040-37-5)

Conditions	Yield
Stage #1: C30H32N6O5*C2H2O4 With potassium carbonate In ethyl acetate at 10 - 15℃; pH=6 - 7; Stage #2: orthocarbonic acid tetraethyl ester In acetic acid at 0 - 25℃; for 15h;	92.3%

orthocarbonic acid tetraethyl ester (78-09-1) + methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (136304-78-4) → methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate (139481-44-0)

Conditions	Yield
With acetic acid at 80 - 90℃; for 0.666667h;	91%
With acetic acid at 80℃; for 1h;	86%
With acetic acid at 78 - 82℃; for 1 - 2h; Heating / reflux; Industry scale;	84.8%
With acetic acid In toluene at 20℃; Reflux;

orthocarbonic acid tetraethyl ester (78-09-1) + 2-nitro-aniline (88-74-4) → 2-ethoxy-1H-benzo[d]imidazole (22219-23-4)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	91%

orthocarbonic acid tetraethyl ester (78-09-1) + C20H16BrN3 → C23H18BrN3O

Conditions	Yield
With acetic acid at 80℃; for 4h;	91%

prednisolon (50-24-8) + orthocarbonic acid tetraethyl ester (78-09-1) → prednisolone-17,21-diethylorthocarbonate (26129-79-3)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane at 22℃; for 17h;	90%

2-cyano-3-methyl-benzenesulfonamide (850154-78-8) + orthocarbonic acid tetraethyl ester (78-09-1) → 2-cyano-N-diethoxymethylene-3-methyl-benzenesulfonamide (937722-17-3)

Conditions	Yield
at 160℃;	90%

orthocarbonic acid tetraethyl ester (78-09-1) + 4-Amino 3-nitro-benzonitrile (6393-40-4) → C10H9N3O (952511-49-8)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	90%

methyl 5-amino-2-furoate (22600-30-2) + orthocarbonic acid tetraethyl ester (78-09-1) → N-(5-methoxycarbonyl-2-furyl)imidocarbonate (110189-96-3)

Conditions	Yield
With trifluoroacetic acid at 80℃; for 24h;	88%

orthocarbonic acid tetraethyl ester (78-09-1) + methyl 3-amino-2-<<(11-cyano-5-oxo-5H-dibenzocyclohepten-3-yl)methyl>amino>benzoate (169270-81-9) → methyl 3-<(11-cyano-5-oxo-5H-dibenzocyclohepten-3-yl)methyl>-2-ethoxy-3H-benzimidazole-4-carboxylate (169270-82-0)

Conditions	Yield
With acetic acid at 100℃; for 2h;	88%

orthocarbonic acid tetraethyl ester (78-09-1) + 3-nitroanthranilic acid (606-18-8) → 2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	88%

orthocarbonic acid tetraethyl ester (78-09-1) + bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-diamine dihydrochloride → (3aα,4α,7α,7aα)-2-ethoxy-3a,4,7,7a-tetrahydro-4,7-methano-1H-benzimidazole

Conditions	Yield
With sodium acetate In acetic acid	87%

orthocarbonic acid tetraethyl ester (78-09-1) + 2,3-Diaminobenzoic acid,ethyl ester (37466-88-9) → ethyl 2-ethoxy-3H-benzimidazole-4-carboxylate (577957-02-9)

Conditions	Yield
With acetic acid at 0 - 20℃; for 3h;	87%

orthocarbonic acid tetraethyl ester (78-09-1) + Methyl 3,4-diaminobenzoate (36692-49-6) → methyl 2-ethoxy-1H-benzo[d]imidazole-6-carboxylate

Conditions	Yield
With acetic acid at 0 - 20℃; for 4h;	87%

trimethylsilyl cyanide (7677-24-9) + orthocarbonic acid tetraethyl ester (78-09-1) → triethoxyacetonitrile (68714-37-4)

Conditions	Yield
tin(IV) chloride for 15h; Ambient temperature;	86%

(R)-3-hydroxybutyric acid (625-72-9) + orthocarbonic acid tetraethyl ester (78-09-1) → β-valerolactone (15890-55-8) + 2,2-dimethoxy-6-methyl-1,3-dioxan-4-one

Conditions	Yield
In benzene	A n/a B 86%

4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (932034-83-8) + orthocarbonic acid tetraethyl ester (78-09-1) → 4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (932035-40-0)

Conditions	Yield
With acetic acid at 20℃; for 4h;	86%

orthocarbonic acid tetraethyl ester (78-09-1) + methyl {(3S)-6-[{(3R)-7-[(2-aminophenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate (1258399-19-7) → methyl [(3S)-6-{[(3R)-7-(2-ethoxy-1H-benzimidazol-1-yl)-2,3-dihydro-1-benzofuran-3-yl](trifluoroacetyl)amino}-2,3-dihydro-1-benzofuran-3-yl]acetate (1258399-22-2)

Conditions	Yield
Stage #1: orthocarbonic acid tetraethyl ester; methyl {(3S)-6-[{(3R)-7-[(2-aminophenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate With acetic acid at 60℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In water	86%

Upstream product

• 56-23-5 tetrachloromethane 
• 141-52-6 sodium ethanolate 
• 60-29-7 diethyl ether 
• 558-13-4 carbon tetrabromide 
• 64-17-5 ethanol 
• 76-06-2 chloropicrin 
• 13029-05-5 trichloro-methanesulfenic acid ethyl ester 
• 594-42-3 chlorothio-trichloro-methane 
• 15146-36-8 N-(di-ethoxymethylene)-benzamide 
• 1122-85-6 phenyl cyanate 
• 545-06-2 trichloroacetonitrile 
• 36749-09-4 3,3-diethoxypentane 
• 68714-37-4 triethoxyacetonitrile 
• 4885-03-4 dichlorodiphenoxymethane 

Downstream Products

• 502-56-7 nonanone-5 
• 96-22-0 pentan-3-one 
• 565-80-0 2,4-dimethylpentan-3-one 
• 123-19-3 4-heptanone 
• 101-99-5 N-carboethoxyaniline 
• 927-49-1 dipentyl ketone 
• 19549-84-9 3-butyl ketone 
• 1663-61-2 triethoxymethylbenzene 
• 119-61-9 benzophenone 
• 925-93-9 ethyl [2]alcohol 
• 79023-44-2 3,3,3-triethoxy-1-phenyl-1-propyne 
• 6263-08-7 Diethyl(phenylimido)carbonat 
• 603-54-3 N,N-diphenylurea 
• 101-01-9 N,N',N''-triphenylguanidine 

Relevant articles and documents

Method for efficiently rectifying and producing tetraethyl orthocarbonate

The invention relates to the field of refining chemicals and specifically relates to a method for efficiently rectifying and producing tetraethyl orthocarbonate. According to the method, a low-polarity inert solvent is used for treating tetraethyl orthocarbonate, so that the extracting function is achieved, less water can be co-boiled and brought away in a rectifying process and the product is prevented from degrading in the rectifying process; the solid alkali is added, so that the pH value of the rectifying system is increased and the product is prevented from continuously degrading under the effect of pH value decreasing in the rectifying process; the technical measure is adopted for acquiring the efficiently rectified and stably produced high-purity tetraethyl orthocarbonate. Comparedwith the present technology, the method provided by the invention has the characteristics of high efficiency, stability, and the like, the high-purity product can be continuously rectified and separated and the purity of the product can reach up to 99.5% or above.

A method for synthesizing original ester carbonate (by machine translation)

The invention relates to a synthesis method of carbonic acid ortho-ester. The synthesis method of the carbonic acid ortho-ester comprises the following steps: (1) preparing crude carbonic acid ortho-ester from tetrahalomethane under the action of alcohol and an alkali metal hydroxide or an alkali metal compound of alcohol, wherein a synthesis reaction equation of the carbonic acid ortho-ester is described in the specification; (2) filtering and removing halide, so that a carbonic acid ortho-ester-alcohol solution is obtained; and (3) carrying out reduced pressure rectification, so that refined carbonic acid ortho-ester is obtained. The synthesis method of the carbonic acid ortho-ester has the advantages that the operation is simple, virulent raw materials and auxiliary materials or auxiliary materials capable of producing highly toxic substances in the traditional technology are abandoned, the emission of three wastes and the cost are greatly reduced, environmental friendliness is realized, and the synthesis method of the carbonic acid ortho-ester is applicable to large-scale production.

Mechanistic study of the ring-size modulation in Michael-Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal

An unexpected modulation of the chemoselectivity in the Michael-Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal is observed, depending on the nature of the acylamino group. Experimental and theoretical studies are presented to offer insights into the origin of this substituent effect in terms of a polar stepwise mechanism. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Process for the preparation of orthocarbonates

Orthocarbonates are prepared by a process, comprising: reacting trichloroacetonitrile with an alkali metal salt or alkaline earth metal salt of an alcohol of the formula: R—OH??(II) wherein R is an unsubstituted or substituted, saturated aliphatic or cycloaliphatic hydrocarbon radical in which the carbon atom of group R, linked to the oxygen atom of the alcohol, has at least one hydrogen atom, reacting the product obtained in water with an oxidant, extracting the organic-aqueous phase of the material obtained after oxidation, and distilling the extracted material obtained and obtaining orthocarbonate product of the formula: C(OR)4??(I) wherein each R group is as defined above.

CRYSTAL AND PROCESS FOR PRODUCING THE SAME

A process for producing crystals of 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimdazole-7-carboxylic acid (compound (I)), characterized by dissolving or suspending the compound (I) or a salt thereof in a solvent comprising an aprotic polar solvent and crystallizing it. By the process, the contaminants which are contained in the compound (I) or its salt and are difficult to remove, such as tin compounds, analogues of the compound (I), and a residual organic solvent, can be easily removed. Crystals of the compound (I) can be efficiently and easily mass-produced in high yield on an industrial scale.

Photopolymerizable vinyl ether based monomeric formulations and polymerizable compositions which may include certain novel spiroorthocarbonates

Photopolymerizable compositions are provided which are the reaction products of a vinyl ether, a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound. These monomeric/oligomeric compositions may also include epoxides, polyols, spiroorthocarbonates. One embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, a spiroorthocarbonate, and a photoinitiator system. Another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, and a photoinitiator system. Still another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, a spiroorthocarbonate, and a photoinitiator system. Still further, another embodiment of the present invention is certain novel spiroorthocarbonate compounds. Each of these novel spiroorthocarbonate compounds include at least one epoxy group as a substituent.

Silver(I) ion-mediated desulfurization-condensation of carbon disulfide with some hydroxyl compounds

The title reaction with ethanol and phenol gave tetraethyl and tetraphenyl orthocarbonate, respectively, in good yields. Diols, such as benzene-1,2-dimethanol, wieso-hydrobenzoin, and cathecol, afforded spiro orthocarbonic acid esters. In the same manner, 2-anilinoethanol, N-methylanthranilic acid, and salicylic acid led to some novel spirobicycles.

Ein neuer Zugang zu Spiroorthocarbonaten und neuen Orthokohlensaeure-Derivaten

New and simple processes have been developed, which give in good or excellent yields new diphenoxyalkanediyldioxymethanes, symmetrical and unsymmetrical spiroorthocarbonates, spirocyclic orthothiocarbamic acid esters, and acetals of urea by successive or simultaneous substitution of chloro and phenoxy groups contained in dichlorodiphenoxymethane.