5754-34-7

Basic information

• Product Name: 4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
• Synonyms: 4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE;(RAC)-2-(2,2-DIMETHYL[1,3]DIOXOLANE-4YL)ETHANOL;4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIO&;2,2-dimethyl-1,3-dioxolane-4-ethanol;1,3-Dioxolane-4-ethanol, 2,2-diMethyl-;4-(2-Hydroxyethyl)-2,2-diMethyl-1,3-dioxolaMe;4-(2-Hydroxyethyl)-2,2-diMethyl-1,3-dioxolane 98%;2-(2,2-Dimethyl-1,3-dioxolan-4-yl)
• CAS NO: 5754-34-7
• Molecular Formula: C₇H₁₄O₃
• Molecular Weight: 146.18
• Mol File: 5754-34-7.mol
• Article Data: 58

Chemical Properties

• Boiling Point: 199-200 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.031 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.7E-15mmHg at 25°C
• Refractive Index: n20/D 1.4400(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.80±0.10(Predicted)
• CAS DataBase Reference: 4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE(5754-34-7)
• EPA Substance Registry System: 4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE(5754-34-7)

Safety Data

• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 5754-34-7(Hazardous Substances Data)

Usage

Uses

2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethanol is used in preparation of cationic lipids and stealth lipids for treating a variety of disorders.

InChI:InChI=1/C27H28ClNO5/c1-5-34-27(31)24-15(2)29-20-12-18(16-6-9-19(28)10-7-16)13-21(30)26(20)25(24)17-8-11-22(32-3)23(14-17)33-4/h6-11,14,18,25,29H,5,12-13H2,1-4H3

Synthetic route

D,L-1,2,4-butanetriol (3068-00-6) + acetone (67-64-1) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 4h;	98%
With toluene-4-sulfonic acid at 20℃; for 20h;	97%
With toluene-4-sulfonic acid	86%

4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane (167629-45-0) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water	90%

D,L-1,2,4-butanetriol (3068-00-6) + 2,2-dimethoxy-propane (77-76-9) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With camphor-10-sulfonic acid	85%
With camphor-10-sulfonic acid In acetonitrile at 20℃;	80%
Stage #1: D,L-1,2,4-butanetriol; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20℃; for 4h; Reflux; Stage #2: In methanol at 0℃; for 12h;	74%

methylene chloride (CH2 Cl2) + para-toluene sulfonic acid (p-TsOH) + D,L-1,2,4-butanetriol (3068-00-6) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With magnesium sulfate In methanol; water; acetone	75%

tert-butyl-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-dimethyl-silane → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.25h;	72%

D,L-1,2,4-butanetriol (3068-00-6) + 2-Methoxypropene (116-11-0) → (2,2-dimethyl-[1,3]dioxan-4-yl)-methanol (56476-33-6) + 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 2-(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)-2-methoxypropane + 2-(2,2-dimethyl-1,3-dioxan-4-ylmethoxy)-2-methoxypropane + 2,2-bis(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)propane

Conditions	Yield
With butyltin(IV) chloride dihydroxide for 90h; Product distribution; Ambient temperature; var. of reagent, ratio, time, further with 2,2-dimethoxypropane;	A 3.0 g B 13.3 g C n/a D n/a E 0.4 g

2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde (83141-42-8) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
reduction;

D,L-1,2,4-butanetriol (3068-00-6) + 2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With toluene-4-sulfonic acid

D,L-1,2,4-butanetriol (3068-00-6) + acetone (67-64-1) → (2,2-dimethyl-[1,3]dioxan-4-yl)-methanol (56476-33-6) + 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
toluene-4-sulfonic acid Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With toluene-4-sulfonic acid Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D,L-1,2,4-butanetriol (3068-00-6) + 2,2-dimethoxy-propane (77-76-9) → (2,2-dimethyl-[1,3]dioxan-4-yl)-methanol (56476-33-6) + 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With pyridinium p-toluenesulfonate In acetone at 20℃; for 0.5h;

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + methanesulfonyl chloride (124-63-0) → 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate (76099-47-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	100%
With triethylamine In toluene at 20℃; for 4h; mesylation;	94%
With triethylamine In dichloromethane at 0℃; for 1.5h;	91%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + p-toluenesulfonyl chloride (98-59-9) → 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate (55559-75-6)

Conditions	Yield
With dmap; triethylamine In dichloromethane 1) 0-5 deg C, 3.5 h; 2) rt, 6 h;	99%
With pyridine 1.) 0 deg C, 2 h, 2.) -20 deg C, overnight;	87%
With pyridine at 0 - 20℃; for 24h;	81%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + allyl bromide (106-95-6) → (±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	98%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) → 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde (83141-42-8)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane Ambient temperature;	93%
With aluminum oxide; pyridinium chlorochromate In dichloromethane at 0 - 20℃;	75%
With camphor-10-sulfonic acid; pyridinium chlorochromate In dichloromethane for 3h;	74%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + benzyl bromide (100-39-0) → (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane (94426-71-8)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	91%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide for 3h; Ambient temperature;	71%
With sodium hydride 1.) DMF, RT, 0.5 h, 2.) 30 deg C, 1.5 h; Yield given. Multistep reaction;

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → 4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane (167629-45-0)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane	91%
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 12h;	91%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 3-chloroprop-1-ene (107-05-1) → (±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Conditions	Yield
With sodium hydroxide In toluene at 30℃; for 6h;	90%
With sodium hydroxide at 30℃; for 2h;

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + oleoyl chloride → (Z)-Octadec-10-enoic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Conditions	Yield
With dmap; TEA for 6h; Ambient temperature;	88%

2,3-dihydro-2H-furan (1191-99-7) + 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) → 2,2-dimethyl-4-[2-(tetrahydro-furan-2-yloxy)-ethyl]-[1,3]dioxolane

Conditions	Yield
With indium(III) chloride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 3h;	87%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 12h;	75%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 4-(dimethylamino)benzenesulfonyl chloride (19715-49-2) → rac-O-isopropylidene-3,4-dihydroxybutyl p-dimethylaminobenzenesulfonate

Conditions	Yield
With pyridine at 4℃; for 72h; Tosylation;	86%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + methanesulfonyl chloride (124-63-0) → 4-(2-methanesulfonylethyl)-2,2-dimethyl-1,3-dioxolane

Conditions	Yield
With triethylamine In dichloromethane at -5℃; for 2.5h; Inert atmosphere;	84.1%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + methanesulfonyl chloride (124-63-0) → 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate (76099-47-3)

Conditions	Yield
With triethylamine In dichloromethane at -5℃; for 2.5h; Inert atmosphere;	84.1%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 2-(phenylsulfonyl)tetrahydro-2H-pyran (96754-03-9) → 2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tetrahydro-pyran (120346-89-6)

Conditions	Yield
With sodium hydrogencarbonate; magnesium bromide In tetrahydrofuran Ambient temperature; overnight (15-24 hrs);	78%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + N-3-benzoylthymine (4330-20-5) → (RS)-1-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethyl]thymine (471256-49-2)

Conditions	Yield
With polystyrene-triphenylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu condensation;	67%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) + perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride (2641-34-1) → C16H13O6F17

Conditions	Yield
With sodium fluoride at 20℃; for 20h;	67%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 4-chloro-2,3-dimethylpyridine-N-oxide (59886-90-7) → 4-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-2,3-dimethylpyridine 1-oxide (1020733-19-0)

Conditions	Yield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 4-chloro-2,3-dimethylpyridine-N-oxide In dimethyl sulfoxide at 60℃; for 2h;	63.8%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) → [2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethoxymethyl]-phosphonic acid diisopropyl ester (918795-56-9)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 16h;	59%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (765962-75-2) → 3-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (1084333-27-6)

Conditions	Yield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In tetrahydrofuran for 0.166667h; Stage #2: 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline In tetrahydrofuran for 0.5h;	59%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + Methacryloyl chloride (920-46-7) → 2-(2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methacrylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;	58.4%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 2,4-Dinitrofluorobenzene (70-34-8) → (+/-)-1,2-O-isopropylydene-4-(2,4-dinitrophenyloxy)-1,2-butanediol (40742-25-4)

Conditions	Yield
With triethylamine at 25℃; for 6h;	58%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) → 4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (98095-37-5)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine at 0 - 20℃; Darkness;	49%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.666667h; Sealed tube; Inert atmosphere;	44%
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: NaI; K2CO3 View Scheme

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) → isopropylidene ketal of rac-3,4-dihydroxybutyl bromide (89942-18-7)

Conditions	Yield
With bromine; triphenylphosphine In N,N-dimethyl-formamide for 1h; Ambient temperature;	48%
With Bromoform; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 20h;	47.8%
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2.5 h / -5 °C / Inert atmosphere 2: magnesium bromide ethyl etherate / diethyl ether / Inert atmosphere View Scheme

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + piperidinophosphoramidic dichloride → [2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl] piperidinophosphoramidate

Conditions	Yield
With n-butyllithium In tetrahydrofuran	43%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 2-fluro-4-iodoaniline (29632-74-4) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-4-fluoro-6-[(2-fluoro-4-iodophenyl)amino]benzonitrile (1084333-29-8)

Conditions	Yield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane; 2,4,6-trifluorobenzonitrile With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 2-fluro-4-iodoaniline With potassium tert-butylate at 20℃; for 3h;	32%

Upstream product

• 3068-00-6 D,L-1,2,4-butanetriol 
• 77-76-9 2,2-dimethoxy-propane 
• 70005-88-8 (R)-1,2,4-butanetriol 
• 67-64-1 acetone 
• 322765-15-1 (E)-ethyl 4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 83141-42-8 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde 
• 97-67-6 L-malic acid 
• 115114-86-8 3,4-O-isopropylidene-L-(S)-erythrulose 
• 92973-40-5 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 116556-67-3 Methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-L-threonate 
• 126946-55-2 ethyl (2rac,3S)-3,4-O-isopropylidene-2-chloro-3,4-dihydroxybutane 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 
• 126946-53-0 ethyl (2R,3S)-3,4-O-isopropylidene-2-p-toluenesulfonyl-3,4-dihydroxybutanoate 
• 91274-05-4 (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 

Downstream Products

• 89942-18-7 isopropylidene ketal of rac-3,4-dihydroxybutyl bromide 
• 167629-45-0 4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane 
• 118806-19-2 benzoic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 1426425-62-8 N-tertbutyl-2-(5-(difluoromethoxy)-1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide 
• 1426425-82-2 N-tert-butyl-2-(1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)-6-fluoro-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide 
• 55559-75-6 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate 
• 55559-76-7 rac-4-(2-chloroethyl)-2,2-dimethyl-1,3-dioxolane 
• 159517-86-9 (R)-(+)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 132278-56-9 (E)-5-Phenyl-pent-4-ene-1,2-diol 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 

Relevant articles and documents

Studies on the cholinergic receptor. 6. Synthesis and muscarinic activity of 2-methyl-4-(2-dimethylaminoethyl)-1,3-dioxolane methiodide.

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