77-76-9

Basic information

• Product Name: 2,2-Dimethoxypropane
• Synonyms: Propane, 2,2-dimethoxy-;Propane,2,2-dimethoxy-;2,2-DIMETHOXYPROPANE;ACETONE DIMETHYL ACETAL;2 2-DIMETHOXYPROPANE REAGENT GRADE 98%;2,2-DIMETHOXYPROPANE pure;Acetone dimethyl acetal, DMP;C.I. 77769
• CAS NO: 77-76-9
• Molecular Formula: C5H12O2
• Molecular Weight: 104.15
• EINECS: 201-056-0
• Product Categories: Organics;Reagents for Oligosaccharide Synthesis;Biochemistry
• Mol File: 77-76-9.mol
• Article Data: 41

Chemical Properties

• Melting Point: -47 °C
• Boiling Point: 83 °C(lit.)
• Flash Point: 12 °F
• Appearance: Clear colorless/Liquid
• Density: 0.847 g/mL at 25 °C(lit.)
• Vapor Density: 3.59 (vs air)
• Vapor Pressure: 60 mm Hg ( 15.8 °C)
• Refractive Index: n20/D 1.378(lit.)
• Storage Temp.: Flammables area
• Solubility: 180g/l
• Explosive Limit: 31%, 58°F
• Water Solubility: 18 g/100 mL (25 ºC)
• Stability: Stable. Highly flammable - note low flash point. Vapour may form an explosive mixture with air. May form explosive peroxides whe
• BRN: 635678
• CAS DataBase Reference: 2,2-Dimethoxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethoxypropane(77-76-9)
• EPA Substance Registry System: 2,2-Dimethoxypropane(77-76-9)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36-36/37/38
• Safety Statements: 26-9-37/39-33-16-33,37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 2
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 77-76-9(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 77-76-9 differently. You can refer to the following data:
1. 2,2-Dimethoxypropane(DMP) is used in histology and considered to be more efficient than ethanol for the dehydration of animal tissue.
2. 2,2-Dimethoxypropane acts as a dehydrating agent. It also serves as an intermediate in the synthesis of vitamin E, vitamin A and various carotenoids such as astaxanthin. It is used as a reagent for the preparation of 1,2-diols, acetonides, isopropylidene derivatives of sugars, nucleosides, methyl esters of amino acids and enol ethers.

General Description

2,2-Dimethoxypropane is an organic compound, which may be used as a protecting agent in the process of the synthesis of structurally related alkaloids like narciclasine and lycoricidine using phenylbromide as the starting material.

Synthetic route

methanol (67-56-1) + 2-bromo-2-nitropropane (5447-97-2) + sodium methylate (124-41-4) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 40℃; for 5h; Irradiation;	96%
at 40℃; for 5h; Product distribution; Irradiation; further primary alcohols;	96%

acetone (67-64-1) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 20℃; for 0.25h; Green chemistry;	95%

pyridoxal hydrochloride (58-56-0) → 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With sulfuric acid In dichloromethane for 6h; Heating; Title compound not separated from byproducts;	A n/a B 92%

2,2,4-trimethyl-1,3-dioxolane (1193-11-9, 116944-25-3) + methanol (67-56-1) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With aluminum (III) chloride at 70℃; for 5.6h; Temperature;	91%

cyclopenta-1,3-diene (542-92-7) + crotonaldehyde (123-73-9) → (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde (153380-53-1) + C9H12O + (1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (249730-06-1) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With 3-(5-(2-(4-benzyl-2,2-dimethyl-5-oxoimidazolidin-1-yl)ethoxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide; trifluoroacetic acid In methanol at 20℃; Catalytic behavior; Solvent; Reagent/catalyst; Diels-Alder Cycloaddition;	A n/a B n/a C n/a D 88%

methanol (67-56-1) + 2,2-dinitropropane (595-49-3) + sodium methylate (124-41-4) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 40℃; for 12h; Irradiation;	84%
at 40℃; for 12h; Product distribution; Irradiation; further primary alcohols;	84%

methanol (67-56-1) + α-nitroisopropyl phenyl sulfone (41774-06-5) + sodium methylate (124-41-4) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 40℃; for 5h; Irradiation;	82%
at 40℃; for 5h; Product distribution; Irradiation; further primary alcohols;	82%

methanol (67-56-1) + 5-t-Butylperoxycyclo-octene → t-butyl bromide (507-19-7) + trans-2-bromo-9-oxabicyclo<4.2.1>nonane (32654-19-6, 89071-84-1, 92617-21-5) + trans-2-bromo-9-oxabicyclo<3.3.1>nonane (32654-27-6, 89071-85-2, 92617-22-6) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With N-Bromosuccinimide for 0.75h; Product distribution; Mechanism; further in CD3OD;	A 1.5% B n/a C n/a D 74%

methanol (67-56-1) + 2-azido-2-nitropropane (85620-94-6, 107494-71-3) + sodium methylate (124-41-4) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 40℃; for 24h; Irradiation;	74%
at 40℃; for 24h; Product distribution; Irradiation; further primary alcohols;	74%

methyl 5-deoxy-5-C-(diethoxyphosphinyl)-2,3-O-isopropylidene-β-D-ribofuranoside (90593-00-3) → 2,2-dimethoxy-propane (77-76-9) + methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside (194412-32-3)

Conditions	Yield
With methanol; iodine for 4.5h;	A n/a B 73%

12,12-dimethoxy-5,5-dimethyl-4,6-dioxatricyclo<7.2.1.02,8>dodec-10-ene (97581-38-9) → endo-7,7-dimethoxy-2,3-bis-hydroxymethylbicyclo[2.2.1]hept-5-ene (122601-54-1) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With toluene-4-sulfonic acid In methanol Heating;	A 68% B n/a

methanol (67-56-1) + acetone (67-64-1) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With formylmorpholine-dimethylsulfate-adduct for 24h; Ambient temperature;	52.9%
With formylmorpholine-dimethylsulfate-adduct for 24h; Product distribution; Ambient temperature; var. other 1-dialkylamino-1-methoxycarbenium methyl sulfates; var. carbonyl compounds; rate of dimethyl ketal formation;	52.9%
AMBERLYST A 15; AMBERLITE IRA 96 at -36 - -34℃; Neat liquid(s);	44.9%

2,2-dimethyl-1,3-dioxolane (2916-31-6) + Cu(CF3SO3)2 + Trimethyl borate (121-43-7) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
	50.31%

2,2-dimethyl-1,3-dioxolane (2916-31-6) + Cu(CF3 SO3)2 + Trimethyl borate (121-43-7) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
	50.31%

methanol (67-56-1) + 1-methyl-1-nitroethyl p-chlorophenyl sulphide (52755-34-7) + sodium methylate (124-41-4) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 40℃; for 2h; Irradiation;	11%
at 40℃; for 2h; Product distribution; Irradiation; further primary alcohols;	11%

methanol (67-56-1) + di-isopropyl ether (108-20-3) → 2-methoxy-2-i-propyloxypropane (87025-34-1) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With potassium hydroxide; tris (2,4-dibromophenyl)amine; lithium perchlorate at 40℃; electrochem. oxidation;	A 0.03% B 3.6%
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation;	A 3% B 0.5%

methanol (67-56-1) + Isopropenyl acetate (108-22-5) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With boron fluoride ether; mercury(II) oxide
With boron fluoride ether; mercury(II) diacetate

methanol (67-56-1) + 1,2-propanediene (463-49-0) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With boron fluoride ether; mercury(II) oxide at 40℃;

methanol (67-56-1) + tetramethylorthosilicate (681-84-5) + acetone (67-64-1) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With phosphoric acid

tetramethylorthosilicate (681-84-5) + acetone (67-64-1) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With hydrogenchloride; methanol
With sulfuric acid

formimidomethylester hydrochloride (15755-09-6) + acetone (67-64-1) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With methanol

methanol (67-56-1) + prop-1-yne (74-99-7) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With boron trifluoride diethyl etherate; mercury(II) oxide
With methyl(triphenylphosphine)gold(I); methanesulfonic acid at 40℃;

methanol (67-56-1) + 1,2-propanediene (463-49-0) → 2-Methoxypropene (116-11-0) + 2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1)

Conditions	Yield
sodium hydroxide at 190℃; Rate constant; other temperatures;

methanol (67-56-1) + t-butyl heptafluoroperoxybutyrate (91481-65-1) → tert.-butylhydroperoxide (75-91-2) + methyl heptafluorobutyrate (356-24-1) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 40℃; for 3h; Yield given. Yields of byproduct given;
In methanol at 10 - 40℃; for 3h; Rate constant; Kinetics; Thermodynamic data; ΔH(act.), ΔS(act.), various temperature;

1,1-dimethoxycyclopropane (29328-23-2) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Product distribution;

t-butyl heptafluoroperoxybutyrate (91481-65-1) → heptafluorobutyric Acid (375-22-4) + 2-Methoxypropene (116-11-0) + tert-butyl heptafluorobutyrate (425-24-1) + 2,2-dimethoxy-propane (77-76-9) + 1-methoxy-1-methylethyl heptafluorobutyrate

Conditions	Yield
In nitrobenzene at 70℃; for 7h; Product distribution;	A 0.90 % Turnov. B 0.19 % Turnov. C 0.02 % Turnov. D 0.06 % Turnov. E 0.05 % Turnov.

acetone (67-64-1) + trimethyl orthoformate (149-73-5) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With ammonium nitrite In methanol for 8h; Heating;
With sulfuric acid In methanol at 20℃;
With sodium montmorillonite In neat (no solvent) at 60℃; for 0.25h; Microwave irradiation; Green chemistry;
With toluene-4-sulfonic acid In methanol Reflux; Molecular sieve;

methanol (67-56-1) + prop-1-yne (74-99-7) → 2-Methoxypropene (116-11-0) + 2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1)

Conditions	Yield
sodium hydroxide at 190℃; Rate constant; other temperatures;

methanol (67-56-1) + 2-bromo-2-nitropropane (5447-97-2) + potassium methanolate (865-33-8) → 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
at 35℃; Product distribution; Mechanism; Irradiation; initial kinetic chain lengths; further alkoxides; with or without (t-Bu)2NO. or oxygen;

3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one (50603-71-9) + 2,2-dimethoxy-propane (77-76-9) → methyl 2-methylazulene-1-carboxylate (54654-48-7)

Conditions	Yield
In toluene at 200℃; for 24h;	100%
In toluene at 200℃;	100%
at 160 - 190℃;	92%

2-Chloroadenosine (146-77-0) + 2,2-dimethoxy-propane (77-76-9) → ((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (24639-06-3)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; Cycloaddition;	100%
With perchloric acid In water at 20℃; for 8h; Reagent/catalyst; Inert atmosphere;	88%
With toluene-4-sulfonic acid In acetone at 45℃;	85%

1-thiophenyl-β-D-galactopyranoside (16758-34-2) + 2,2-dimethoxy-propane (77-76-9) → phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside (270075-72-4)

Conditions	Yield
With camphor-10-sulfonic acid at 20℃; for 24h;	100%
With scandium tris(trifluoromethanesulfonate) In acetone at 23℃; for 0.5h; Addition;	86%
With toluene-4-sulfonic acid In water at 20℃; for 4h;	76%

methyl 6-azido-6-deoxy-α-D-mannopyranoside (66224-56-4) + 2,2-dimethoxy-propane (77-76-9) → methyl 6-azido-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside (120138-99-0)

Conditions	Yield
With CSA at 20℃; for 3h;	100%
With toluene-4-sulfonic acid for 1.5h; Ambient temperature;	97%
With toluene-4-sulfonic acid In acetone at 20℃; for 18h; Inert atmosphere;	78%
camphor-10-sulfonic acid at 20℃; for 1h;

L-arabinose di(ethylthio)acetal (43179-48-2) + 2,2-dimethoxy-propane (77-76-9) → (4R,5S)-4-(bis(ethylthio)methyl)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolane (92936-93-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 5h;	100%
With phosphorus pentoxide In acetone	92%
With phosphorus pentoxide In acetone at 40℃; for 0.25h;	85%
With toluene-4-sulfonic acid In acetone 1.) RT, 30 min, 2.) 40 deg C, 2 h;

diethyl (2R,3R)-tartrate (87-91-2) + 2,2-dimethoxy-propane (77-76-9) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) + (4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 8h; Heating; Title compound not separated from byproducts.;	A 100% B n/a
for 2.5h; Heating;

2-Methoxypropene (116-11-0) + 2,2-dimethoxy-propane (77-76-9) + 4-Hydroxy-2-((Z)-8-hydroxy-7-oxo-oct-2-enyl)-cyclopent-2-enone → 2-[(Z)-6-(4-Methoxy-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-2-enyl]-4-(1-methoxy-1-methyl-ethoxy)-cyclopent-2-enone

Conditions	Yield
With toluene-4-sulfonic acid	100%

diethyl bis(hydroxymethyl)malonate (20605-01-0) + 2,2-dimethoxy-propane (77-76-9) → 2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester (51335-75-2)

Conditions	Yield
With APTS*H2O at 20℃; for 17h;	100%
With sulfuric acid In acetone at 20℃; for 19h;	94%
With toluene-4-sulfonic acid In acetone for 6h; Heating;	90%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + 2,2-dimethoxy-propane (77-76-9) → N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine (117833-99-5)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1h; Heating;	100%
With toluene-4-sulfonic acid	99%
With toluene-4-sulfonic acid In benzene for 1h; Heating;	97%

(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol (108393-28-8) + 2,2-dimethoxy-propane (77-76-9) → (2S,3S,4S)-5-Benzyloxy-1,3-isopropylidenedioxy-2,4-dimethylpentane (81470-77-1, 98102-72-8, 100760-30-3, 115181-74-3, 133006-91-4, 135211-99-3, 138124-14-8, 145514-09-6)

Conditions	Yield
With toluene-4-sulfonic acid for 5.5h;	100%

(7S,13E,16S,17R,18R)-2-Benzoyl-7-tert-butyldimethylsilyloxy-17,18-dihydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13-diene-1,21-dione (129056-37-7) + 2,2-dimethoxy-propane (77-76-9) → (7S,13E,16S,17R,18R)-2-Benzoyl-7-tert-butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13-diene-1,21-dione (129056-38-8)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform	100%
With toluene-4-sulfonic acid In chloroform at 20℃; for 5h; Cyclization; Etherification;	99%

(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol (85148-25-0) + 2,2-dimethoxy-propane (77-76-9) → (S)-4-<2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl>-2,2,4-trimethyl-1,3-dioxorane (69821-03-0)

Conditions	Yield
With toluene-4-sulfonic acid for 0.25h; Ambient temperature;	100%
toluene-4-sulfonic acid optical purity more than 95percent;

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) + 2,2-dimethoxy-propane (77-76-9) → methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6, 95715-86-9)

Conditions	Yield
With boron trifluoride diethyl etherate In acetone	100%
With boron trifluoride diethyl etherate In acetone at 20℃; for 3.5h;	92%
With boron trifluoride diethyl etherate In acetone at 20℃; for 2h;	91%

threo (2S,3R)-3-(4-methoxyphenyl)-1,1-bis(p-tolylthio)propane-2,3-diol (130718-72-8) + 2,2-dimethoxy-propane (77-76-9) → (4S,5R)-trans-4--5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan (130796-28-0)

Conditions	Yield
With toluene-4-sulfonic acid Ambient temperature;	100%

(2S,3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-5-ene-2,4-diol (180628-57-3) + 2,2-dimethoxy-propane (77-76-9) → tert-Butyl-diphenyl-((4S,5S,6R)-2,2,5-trimethyl-6-vinyl-[1,3]dioxan-4-ylmethoxy)-silane (180628-58-4)

Conditions	Yield
	100%

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1, 82683-92-9, 132958-32-8, 130792-45-9) + 2,2-dimethoxy-propane (77-76-9) → (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9)

Conditions	Yield
With toluene-4-sulfonic acid	100%
toluene-4-sulfonic acid at 18℃; for 1h;	99%
With toluene-4-sulfonic acid In acetone at 20℃; for 0.5h;	98%

(S)-3-Benzylsulfanyl-propane-1,2-diol (131164-81-3) + 2,2-dimethoxy-propane (77-76-9) → (-)-(S)-(2,3-isopropylidenedioxy)propyl benzyl sulfide (192999-30-7)

Conditions	Yield
With toluene-4-sulfonic acid Ambient temperature;	100%

2,2-dimethoxy-propane (77-76-9) + D-Ribono-1,4-lactone (5336-08-3) → 2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9)

Conditions	Yield
With hydrogen cation In acetone	100%
With boron trifluoride diethyl etherate In acetone at 20℃; for 1.5h; Condensation;	90%
With boron trifluoride diethyl etherate In acetone at 20℃; Inert atmosphere;	86%

5,6-exo-dihydroxy-2-(N-methylcarbamoyl)-2-azabicyclo<2.2.1>heptan-3-one (124575-00-4) + 2,2-dimethoxy-propane (77-76-9) → 5,6-exo-dimethylmethylenedioxy-2-(N-methylcarbamoyl)-2-azabicyclo<2.2.1>heptan-3-one (124575-01-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetone for 0.666667h; Ambient temperature;	100%
With toluene-4-sulfonic acid In acetone

Methanesulfonic acid (2S,3R,4S,5R)-2-benzyloxymethyl-5-((4S,5R)-5-ethyl-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-3,5-dihydroxy-4-methyl-pentyl ester (114826-03-8) + 2,2-dimethoxy-propane (77-76-9) → Methanesulfonic acid (S)-3-benzyloxy-2-[(4R,5S,6R)-6-((4R,5R)-5-ethyl-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; for 16h;	100%

(2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene (67470-70-6) + 2,2-dimethoxy-propane (77-76-9) → (4R,5R)-2,2,4-Trimethyl-5-((E)-1-methyl-2-phenyl-vinyl)-[1,3]dioxolane (81653-01-2)

Conditions	Yield
With toluene-4-sulfonic acid In benzene	100%

4-(R,S)-(t-butoxycarbonylamino)-3-oxo-1,2-diazolidine (106693-44-1) + 2,2-dimethoxy-propane (77-76-9) → C11H19N3O3 (106893-80-5)

Conditions	Yield
camphor-10-sulfonic acid In methanol for 1h; Heating;	100%

(3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane (153025-58-2) + 2,2-dimethoxy-propane (77-76-9) → (3S,5S)-6-<(benzyloxy)methyl>-4-<1-(tert-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxacyclohexane (112497-22-0)

Conditions	Yield
With camphor-10-sulfonic acid for 1h;	100%
With camphor-10-sulfonic acid	99%

(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((1S,2S)-1,2-dihydroxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (138383-64-9) + 2,2-dimethoxy-propane (77-76-9) → (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4R,5S)-2,2-dimethyl-5-thiazol-2-yl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (138319-94-5)

Conditions	Yield
With o-toluenesulfonic acid; magnesium sulfate; acetone for 4h; Ambient temperature;	100%

(1aR,8R,9aR)-7-Benzyloxy-3-hydroxy-8-hydroxymethyl-5-(4-methoxy-phenoxymethyl)-1a,3,8,9a-tetrahydro-2H-1-oxa-3-aza-benzo[a]cyclopropa[e]cycloocten-9-one + 2,2-dimethoxy-propane (77-76-9) → C30H31NO7 (138008-38-5)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane at 23℃;	100%

DL-(1α,2α,3β,4β,5α,7α)-2,5-Dibrom-8-oxabicyclo<5.1.0>octan-3,4-diol (59992-02-8, 82570-09-0) + 2,2-dimethoxy-propane (77-76-9) → DL-(1α,2α,3β,4β,5α,7α)-2,5-Dibrom-3,4-O-isopropyliden-8-oxabicyclo<5.1.0>octan-3,4-diol (91303-56-9)

Conditions	Yield
With toluene-4-sulfonic acid Heating;	100%

(2R,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,1-bisethylsulfanyl-butane-2,3-diol (108714-02-9) + 2,2-dimethoxy-propane (77-76-9) → 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythrose diethyl dithioacetal (105265-86-9)

Conditions	Yield
With (1S)-10-camphorsulfonic acid In acetone for 4h; Ambient temperature;	100%
With toluene-4-sulfonic acid In acetone Yield given;

(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one (81481-12-1) + 2,2-dimethoxy-propane (77-76-9) → (22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide (81481-13-2)

Conditions	Yield
With toluene-4-sulfonic acid	100%
With camphor-10-sulfonic acid In dichloromethane; acetonitrile for 1h; Ambient temperature;	98%
With toluene-4-sulfonic acid In dichloromethane for 1h; Ambient temperature; Yield given;

(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropane-1,2-diol (109240-70-2) + 2,2-dimethoxy-propane (77-76-9) → tert-Butyl-dimethyl-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethoxy)-silane (109240-71-3)

Conditions	Yield
camphor-10-sulfonic acid for 3h; Ambient temperature;	100%

(S)-1-benzyloxy-2-methylpropane-2,3-diol (109240-67-7) + 2,2-dimethoxy-propane (77-76-9) → 4-benzyloxymethyl-2,2,4-trimethyl-1,3-dioxolane (109240-68-8)

Conditions	Yield
camphor-10-sulfonic acid for 3h; Ambient temperature;	100%

Upstream product

• 67-56-1 methanol 
• 108-22-5 Isopropenyl acetate 
• 681-84-5 tetramethylorthosilicate 
• 67-64-1 acetone 
• 74-99-7 prop-1-yne 
• 463-49-0 1,2-propanediene 
• 91481-65-1 t-butyl heptafluoroperoxybutyrate 
• 149-73-5 trimethyl orthoformate 
• 5447-97-2 2-bromo-2-nitropropane 
• 865-33-8 potassium methanolate 
• 124-41-4 sodium methylate 
• 595-49-3 2,2-dinitropropane 
• 85620-94-6 2-azido-2-nitropropane 
• 52755-34-7 1-methyl-1-nitroethyl p-chlorophenyl sulphide 

Downstream Products

• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 116-11-0 2-Methoxypropene 
• 1080-06-4 L-Tyr-OMe 
• 10076-48-9 methyl 2,2-dimethoxypropionate 
• 18271-82-4 chloral methyl hemiacetal 
• 1552-33-6 5,5,5-trichloro-4-hydroxypentan-2-one 
• 35219-73-9 2,2-bis-allyloxy-propane 
• 3900-79-6 toluene-4-sulfonic acid isopropylidenehydrazide 
• 53951-40-9 Aceton-methylpropylketal 
• 35946-83-9 4-amino-5-(tri-O-benzyl-β-D-ribofuranosyl)-1(2)H-pyrazole-3-carboxylic acid methyl ester 
• 2235-01-0 dimethoxydiphenylmethane 
• 73488-22-9 (3aR)-6t-benzyloxycarbonylamino-7c-(2-benzyloxycarbonylamino-O⁴,O⁶-isopropylidene-α-D-ribo-2,3-dideoxy-hexopyranosyloxy)-4c-hydroxy-(3ar,7ac)-hexahydro-benzooxazol-2-one 
• 29328-22-1 Aceton-methylethylketal 
• 126-84-1 2,2-diethoxypropane 

Relevant articles and documents

Pressure Stabilization and Solvation Thermodynamics of a Hemiketal Reaction Intermediate

This work reports the first pressure stabilization of a hemiketal intermediate, 2-methoxy-2 propanol, formed in the reaction of acetone and methanol, observed using Raman spectroscopy. Acetone dissolved in methanol is found to undergo a two-step reaction, with the ketal 2,2-dimethoxy-propane as the final product and the hemiketal observed as an intermediate. In a more dilute stoichiometric mixture of acetone and methanol in liquid tetrahydrofuran (THF), quantitative formation of the hemiketal is observed at pressures above 2 GPa. The complete set of reaction thermodynamic functions (ΔH0, ΔV0, ΔS0, ΔG0, ΔU0, ΔA0) is obtained for the hemiketal formation reaction in THF as a function of temperature and pressure and compared with previous measurements of ΔH0, ΔS0, and ΔG0 for acetone dissolved in methanol. Comparisons with quantum calculations for the isolated reactant and product species are used to completely quantitate the effects of solvation on the hemiketal formation reaction.

Preparation method of 2, 2-dimethoxypropane

The invention discloses a preparation method of 2, 2-dimethoxypropane. The method adopts methanol and acetone as the raw materials, utilizes a metal oxide modified SO4/SnO2 catalyst to catalyze reaction, and includes the reaction steps of: a) subjecting methanol and acetone to preheating vaporization by a preheater respectively, and controlling the preheating temperature at 65-95DEG C; b) letting the vaporized methanol and acetone enter the reactor respectively, and contacting the vaporized methanol and acetone with the metal oxide modified SO4/SnO2 catalyst for catalytic reaction in the reactor at a temperature of 83-95DEG C so as to obtain a crude product containing 2, 2-dimethoxypropane and unreacted methanol and acetone. Specifically, the metal oxide is one of or a mixture of several of Fe2O3, Al2O3 and Ga2O3. The method adopted by the invention is carried out at high temperature, solves the problem of long reaction time at low temperature, has high single conversion rate,and does not introduce new impurities are introduced in the subsequent concentration process.

2,2-dimethoxypropane production method

The invention discloses a 2,2-dimethoxypropane production method. Methanol and acetone are used as raw materials, strong acid cation exchange resin serves as a catalyst, super absorbent resin serves as a dehydrating agent, and a product is obtained through reduced pressure rectification. The super absorbent resin can be recycled after hot air drying, and a mixture of a small quantity of methanol,acetone and 2,2-dimethoxypropane and water after drying can be separated through pressurized condensation, the separated water can be discharged directly, and the separated mixture of methanol, acetone and 2,2-dimethoxypropane are returned to a fixed bed reactor to continue to participate in reaction. The method is simple in process, high in continuity and low in cost, the total yield of productsis high and is greater than 65%, high quality is achieved while the purity is higher than 99%, and a high industrial application value is achieved.