glycolaldehyde dimer
methanol
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
aminopropylated Silica-Gel hydrochloride (APSG*HCl) resin for 15h; Ambient temperature; | 92% |
With hydrogenchloride at 89.84℃; for 1h; Reagent/catalyst; Time; | 72 %Chromat. |
Conditions | Yield |
---|---|
With titanium tetrachloride for 3h; Irradiation; | 68% |
methanol
D-Xylose
A
methyl xyloside
B
2,2-dimethoxyethanol
C
methyl lactate
Conditions | Yield |
---|---|
With Ti-beta zeolite at 160℃; for 2h; Microwave irradiation; | A 48% B 7% C 11% |
With Zr-beta zeolite at 160℃; for 2h; Microwave irradiation; | A 39% B 12% C 10% |
Conditions | Yield |
---|---|
With titanium tetrachloride for 3h; Irradiation; | 37% |
methanol
Glycolaldehyde
A
2,2-dimethoxyethanol
B
glycolic acid methyl ester
C
ethylene glycol
Conditions | Yield |
---|---|
tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | A n/a B n/a C 35% |
With triethylamine; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | A n/a B n/a C 35% |
With potassium carbonate; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 20℃; for 2 - 5h; Product distribution / selectivity; | A n/a B n/a C 27% |
With caesium carbonate; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 20℃; for 2 - 5h; Product distribution / selectivity; | A n/a B n/a C 27% |
With potassium hydroxide; dichloro(pentamethylcyclopentadienyl) iridium In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | A n/a B n/a C 20% |
methanol
D-Xylose
A
furfural
B
2-furaldehyde dimethyl acetal
C
methyl xyloside
D
2,2-dimethoxyethanol
E
methyl lactate
Conditions | Yield |
---|---|
With Sn-beta zeolite at 160℃; for 2h; Microwave irradiation; | A n/a B n/a C 32% D 6% E 11% F 12% |
methanol
D-Xylose
A
methyl xyloside
B
2,2-dimethoxyethanol
C
methyl lactate
Conditions | Yield |
---|---|
With Sn-beta zeolite at 160℃; for 2h; Microwave irradiation; | A 30% B 6% C 17% D 11% |
2-benzyloxy-1,1-dimethoxyethane
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
With diethyl ether; ammonia; sodium |
Conditions | Yield |
---|---|
With hydrogenchloride | |
With S2O82-/silicon MCM-41 at 100℃; for 3h; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid |
Conditions | Yield |
---|---|
(i) Br2, Et2O, (ii) /BRN= 3592982/; Multistep reaction; |
Conditions | Yield |
---|---|
With tetraethylammonium tosylate anodic oxidation; |
methanol
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
With titanium tetrachloride for 15h; Irradiation; Yield given; |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid; sulfuric acid 1a) MeOH, 0 deg C, 1.5h, 1b) RT, overnight, 2) 1h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium hydrogencarbonate; acetonitrile; sulfuric acid 1a) MeOH, 0 deg C, 1.5h, 2) 12h, reflux, 2) MeOH, 1h, reflux; Yield given. Multistep reaction; |
methanol
Glycolaldehyde
A
2,2-dimethoxyethanol
B
glycolic acid methyl ester
Conditions | Yield |
---|---|
dichloro(pentamethylcyclopentadienyl) iridium In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | |
With potassium carbonate; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | |
With caesium carbonate; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | |
With potassium hydroxide; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; | |
With sodium hydroxide; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 70℃; for 2 - 5h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 120℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 5 %Chromat. B 31 %Chromat. |
D-xylose
A
2,2-dimethoxyethanol
B
methyl lactate
C
methyl 2-hydroxybut-3-enoate
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 160℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 5 %Chromat. B 42 %Chromat. C 7 %Chromat. |
D-Arabinose
A
2,2-dimethoxyethanol
B
methyl lactate
C
methyl 2-hydroxybut-3-enoate
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 160℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 6 %Chromat. B 39 %Chromat. C 8 %Chromat. |
D-ribose
A
2,2-dimethoxyethanol
B
methyl lactate
C
methyl 2-hydroxybut-3-enoate
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 160℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 5 %Chromat. B 38 %Chromat. C 8 %Chromat. |
D-lyxose
A
2,2-dimethoxyethanol
B
methyl lactate
C
methyl 2-hydroxybut-3-enoate
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 160℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 6 %Chromat. B 39 %Chromat. C 7 %Chromat. |
Glycolaldehyde
A
2,2-dimethoxyethanol
B
methyl lactate
C
methyl 2-hydroxybut-3-enoate
D
methyl 2-hydroxy-4-methoxybutanoate
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 120℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 7 %Chromat. B 10 %Chromat. C 25 %Chromat. D 19 %Chromat. |
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 140℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 8 %Chromat. B 14 %Chromat. C 30 %Chromat. D 12 %Chromat. |
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 160℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 7 %Chromat. B 16 %Chromat. C 27 %Chromat. D 6 %Chromat. |
Glycolaldehyde
A
2,2-dimethoxyethanol
B
methyl 2-hydroxybut-3-enoate
C
methyl 2-hydroxy-4-methoxybutanoate
Conditions | Yield |
---|---|
With zeotype catalyst Sn-Beta (Si/Sn = 400) In methanol at 100℃; under 15001.5 Torr; for 16h; Autoclave; Inert atmosphere; | A 8 %Chromat. B 13 %Chromat. C 26 %Chromat. |
glycolaldehyde dimer
methanol
A
2,2-dimethoxyethanol
B
methyl 2-hydroxy-4-methoxybutanoate
Conditions | Yield |
---|---|
With tin (IV) chloride pentahydrate at 89.84℃; for 1h; Kinetics; Reagent/catalyst; Time; | A 54 %Chromat. B 10 %Chromat. |
methanol
D-xylofuranose
A
2,2-dimethoxyethanol
B
glycolic acid methyl ester
C
methyl lactate
Conditions | Yield |
---|---|
at 240℃; under 20686.5 Torr; for 1h; Inert atmosphere; |
Conditions | Yield |
---|---|
at 240℃; under 20686.5 Torr; for 1h; Inert atmosphere; |
methanol
Glycolaldehyde
A
2,2-dimethoxyethanol
B
methyl lactate
Conditions | Yield |
---|---|
With mesoporous Zr-SBA-15 at 240℃; under 20686.5 Torr; for 1h; Inert atmosphere; |
Methyl dimethoxyacetate
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; | 5.45 g |
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 4h; | 100% |
2,2-dimethoxyethanol
isobutyryl chloride
isobutyric acid 2,2-dimethoxy-ethyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine at 20℃; for 16h; | 99% |
With dmap; triethylamine In ethyl acetate at 0 - 20℃; for 16h; | 99% |
With dmap; triethylamine In tert-butyl methyl ether at 0 - 20℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 12h; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; | 93% |
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 16h; | 60% |
2,2-dimethoxyethanol
carbon monoxide
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; palladium diacetate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine) In chlorobenzene; acetone at 20 - 80℃; for 30h; Schlenk technique; enantioselective reaction; | 93% |
2,2-dimethoxyethanol
2-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With TEA In dichloromethane at 20℃; for 3h; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 24h; Heating; | 91% |
With hydrogenchloride In ethanol; water at -5℃; for 24h; Reflux; | 91% |
3-thienyl iodide
2,2-dimethoxyethanol
3-(2,2-dimethoxyethoxy)thiophene
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In toluene at 110℃; for 36h; | 91% |
Conditions | Yield |
---|---|
With Montmorillonite K10 at 20℃; for 1.5h; | 88% |
2,2-dimethoxyethanol
2-Fluoro-4-iodo-3-methylpyridine
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethoxyethanol With sodium hydride In tetrahydrofuran Stage #2: 2-Fluoro-4-iodo-3-methylpyridine In tetrahydrofuran at 20℃; Further stages.; | 86% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 120h; | 85% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran -78 deg C -> r.t.; | 82% |
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane for 24h; Ambient temperature; | 81% |
2,2-dimethoxyethanol
sorbinyl chloride
2,2-dimethoxyethyl (2E,4E)-2,4-hexadienoate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 9h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethoxyethanol With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 2-Chloroquinoline In N,N-dimethyl-formamide at 20℃; for 24h; | 81% |
2,6-dichloroquinoline
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethoxyethanol With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 2,6-dichloroquinoline In N,N-dimethyl-formamide at 20℃; for 24h; | 81% |
2,2-dimethoxyethanol
ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside
Conditions | Yield |
---|---|
With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane; toluene at 0℃; | 80% |
2,2-dimethoxyethanol
ethyl-2-O-benzyl-6-O-isopropyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside
Conditions | Yield |
---|---|
With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane; toluene at 0℃; | 80% |
2,2-dimethoxyethanol
N-(2-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-4-nitrobenzenesulfonamide
N-[2-(tert-butyldimethylsilanyloxymethyl)phenyl]-N-(2,2-dimethoxyethyl)-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -20 - 30℃; for 21h; Mitsunobu reaction; | 80% |
3,3-Dimethylacryloyl chloride
2,2-dimethoxyethanol
2,2-dimethoxyethyl 3-methyl-2-butenoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; | 78% |
2,2-dimethoxyethanol
methyl 2-(bromomethyl)propenoate
2-(2,2-dimethoxy-ethoxymethyl)-acrylic acid methyl ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 78% |
indole
2,2-dimethoxyethanol
acetic anhydride
2,2-di-(1H-indol-3-yl)ethyl acetate
Conditions | Yield |
---|---|
Stage #1: indole; 2,2-dimethoxyethanol at 20℃; for 1.5h; Stage #2: acetic anhydride With sodium acetate at 20℃; for 17h; | 76% |
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
With silver carbonate In dichloromethane at 0℃; | 75% |
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
With 4 A molecular sieve; silver carbonate In dichloromethane at 0℃; | 75% |
2,2-dimethoxyethanol
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
Fmoc-Ser(tBu)-OH
4-Nitrobenzenesulfonyl chloride
(3S,6S,8aS)-6-methyl-7-((4-nitrophenyl)sulfonyl)-5-oxohexahydro-2H-oxazolo[3,2-a]pyrazine-3-carboxamide
Conditions | Yield |
---|---|
Stage #1: Fmoc-Ser(tBu)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Rink amide resin; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.333333h; Rink amide resin; Stage #3: 2,2-dimethoxyethanol; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 4-Nitrobenzenesulfonyl chloride stereoselective reaction; Further stages; | 75% |
2,2-dimethoxyethanol
6-chloro-2-(chloromethyl)-1-isopropyl-imidazo [4,5-c]pyridine
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethoxyethanol With sodium hydride In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: 6-chloro-2-chloromethyl-1-isopropyl-1H-imidazo[4,5-c]pyridine In N,N-dimethyl-formamide at 50℃; for 2h; | 75% |
2,2-dimethoxyethanol
monoallyl malonate
bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate | 73% |
2,2-dimethoxyethanol
4-phenylbutyronitrile
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 120h; | 73% |
veratronitrile
2,2-dimethoxyethanol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃; for 24h; Concentration; Solvent; Temperature; | 68% |
The Ethanol, 2,2-dimethoxy-, with the CAS registry number 30934-97-5 and EINECS registry number 250-398-7, has the systematic name and IUPAC name of 2,2-dimethoxyethanol. And the molecular formula of the chemical is C4H10O3. What's more, while dealing with this chemical, you should avoid contacting with skin and eyes, and do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).
The characteristics of Ethanol, 2,2-dimethoxy- are as followings: (1)ACD/LogP: -0.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.41; (4)ACD/LogD (pH 7.4): -0.41; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 14.31; (8)ACD/KOC (pH 7.4): 14.31; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 27.69 Å2; (13)Index of Refraction: 1.401; (14)Molar Refractivity: 25.56 cm3; (15)Molar Volume: 105.1 cm3; (16)Polarizability: 10.13×10-24cm3; (17)Surface Tension: 29.3 dyne/cm; (18)Density: 1.009 g/cm3; (19)Flash Point: 42.2 °C; (20)Enthalpy of Vaporization: 44.63 kJ/mol; (21)Boiling Point: 146.1 °C at 760 mmHg; (22)Vapour Pressure: 1.85 mmHg at 25°C.
Preparation of Ethanol, 2,2-dimethoxy-: This chemical can be prepared by methanol and formic acid methyl ester. The reaction will need reagent titanium(IV) chloride. The reaction time is 3 hours with irridieation, and the yield is about 68%.
Uses of Ethanol, 2,2-dimethoxy-: It can react with 3-methyl-but-2-enoyl chloride to produce 2,2-dimethoxyethyl 3-methyl-2-butenoate. This reaction will need reagent pyridine, and the menstruum CH2Cl2. And the yield is about 78%.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: OCC(OC)OC
(2)InChI: InChI=1/C4H10O3/c1-6-4(3-5)7-2/h4-5H,3H2,1-2H3
(3)InChIKey: NYPNCQTUZYWFGG-UHFFFAOYAP
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