597-31-9

Basic information

• Product Name: 3-Hydroxy-2,2-dimethylpropanal
• Synonyms: 2-(hyroxymethyl)-2-methylpropanal;2,2-dimethyl-3-hydroxy-propana;2,2-dimethyl-3-hydroxypropanal;2,2-dimethyl-3-hydroxypropioaldehyde;2,2-Dimethyl-3-hydroxypropionaldehyde;2,2-dimethyl-beta-hydroxypropionaldehyde;2,2-dimethyl-hydracrylaldehyd;3-hydroxy-2,2-dimethyl-propana
• CAS NO: 597-31-9
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 209-895-4
• Mol File: 597-31-9.mol
• Article Data: 63

Chemical Properties

• Melting Point: 30-33 °C
• Boiling Point: 131.45°C (rough estimate)
• Flash Point: 60.3°C
• Appearance: /
• Density: 0.9571 (rough estimate)
• Vapor Pressure: 0.0632mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), DMSO, Methanol (Slightly), Water (Slightly)
• PKA: 14.25±0.10(Predicted)
• CAS DataBase Reference: 3-Hydroxy-2,2-dimethylpropanal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-2,2-dimethylpropanal(597-31-9)
• EPA Substance Registry System: 3-Hydroxy-2,2-dimethylpropanal(597-31-9)

Safety Data

• Hazardous Substances Data: 597-31-9(Hazardous Substances Data)

Usage

Uses

3-Hydroxy-2,2-dimethylpropanal is used to prepare 4,1-benzoxazepines as squalene synthase inhibitors and their inhibition of cholesterol synthesis. It is also used to prepare chiral cyanohydrins.

InChI:InChI=1/C5H10O2/c1-5(2,3-6)4-7/h3,7H,4H2,1-2H3

Synthetic route

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With water; potassium carbonate at 25℃; Aldol Condensation; Cooling with ice;	92%
With triethylamine In water for 3h; Heating;	91%
With sodium hydroxide at 80℃; for 0.516667h; Temperature; Aldol Condensation;	91.14%

2-methyl-1,2-epoxypropane (558-30-5) + carbon monoxide (201230-82-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
Stage #1: 2-methyl-1,2-epoxypropane With rhodium (II) octanoate dimer; boron trifluoride at 50℃; for 0.5h; Inert atmosphere; Stage #2: carbon monoxide With hydrogen at 90℃; under 75007.5 Torr; Reagent/catalyst; Temperature; Pressure;	90.3%

formaldehyd (50-00-0) + trimethylsilyl propenyl ether (19879-97-1) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 50℃;	85%

formaline + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-dimethyl-3-hydroxypropyl 2-methylpropionate (5919-84-6) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
With triethylamine at 65 - 90℃; for 0.666667h; Nitrogen atmosphere;	A 62.4% B 2% C 0.26% D 0.64%

2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane (219606-56-1) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With acetic acid at 35℃; for 8h;	42%

3-acetoxymethoxy-2,2-dimethyl-propionaldehyde → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With sulfuric acid

potassium cyanide (151-50-8) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,4-dihydroxy-3,3-dimethyl-butyraldehyde (13199-26-3) + 3-Deoxy-3,3-di-C-methyl-DL-glycero-tetrose hydrate + 3-Deoxy-3,3-di-C-methyl-α-DL-glycero-tetrose (103203-99-2, 133094-80-1, 133094-96-9, 134932-06-2, 134932-07-3)

Conditions	Yield
With hydrogen; Pd-BaSO4 1) water, 15 min, pH 7.7 2) pH 1.7; Multistep reaction. Title compound not separated from byproducts;

2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With cyclohexanone; bis(cyclopentadienyl)dihydrozirconium at 150℃; for 8h;	66 % Chromat.
With sodium nitrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver nitrate In water for 7h; Irradiation; regioselective reaction;

2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethylmalonaldehyde (1185-34-8)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethylsulfoxide-d6 at 23℃; Product distribution; product ratio was determined by 1H NMR;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) + potassium carbonate → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

4-hydroxy-5.5-dimethyl-2-<2-hydroxy-1.1-dimethyl-ethyl>-1.3-dioxane → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
under 14 Torr;

hydrogenchloride (7647-01-0) + bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine (59676-94-7) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + hydrazine salt

bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine (59676-94-7) + sulfuric acid (7664-93-9) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + hydrazine salt

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane (46329-82-2, 67081-75-8, 67081-77-0, 87194-52-3) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
In tetrahydrofuran at 65℃; for 3h;
at 26℃; for 28h; pH=2.5; aq. phosphate buffer;
In acetonitrile at 65℃; for 3h; Inert atmosphere;

calcium (R)-pantothenate (137-08-6) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + carbon dioxide (124-38-9) + calcium beta-alaninate (36321-40-1)

Conditions	Yield
With sodium hydroxide; potassium permanganate; sodium perchlorate In water at 25℃; for 8h; Kinetics; Further Variations:; Reagents; Temperatures;

3-hydroxy-4,4-dimethyltetrahydrofuran (15833-82-6) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: aq. H2SO4 View Scheme

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-dimethyl-3-hydroxypropyl 2-methylpropionate (5919-84-6) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
triethylamine at 40 - 90℃; for 0.666667h; Aldol Condensation;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → formic acid (64-18-6) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
triethylamine In water Product distribution / selectivity; Aldol Condensation;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
With triethylamine In water at 40 - 90℃; for 0.666667h;
With triethylamine In water at 40 - 90℃; for 0.666667h;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane (46329-82-2, 67081-75-8, 67081-77-0, 87194-52-3) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With potassium carbonate In water at 0 - 20℃;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → methanol (67-56-1) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With triethylamine

formaldehyd (50-00-0) + isovaleraldehyde (590-86-3) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
Aldol condensation;

methanol (67-56-1) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 3-Hydroxy-2,2-dimethylpropanoic acid (4835-90-9) + Methyl 2,2-dimethyl-3-hydroxypropionate (14002-80-3)

Conditions	Yield
With 1% Au-Pd/TiO2; oxygen; sodium hydroxide at 80℃; under 2250.23 Torr; for 4h;

formaldehyd (50-00-0) + 2,2'-iminobis[ethanol] (111-42-2) + isovaleraldehyde (590-86-3) → 2-(oxazolidin-3-yl)ethanol (20073-50-1) + N-(2-hydroxyethyl)-2-isopropyloxazolidine (28770-01-6) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 3-(N,N-bis(2-hydroxyethyl)amino)-2,2-dimethylpropanal (1122612-55-8)

Conditions	Yield
In water at 80℃; for 2h; Inert atmosphere; Cooling;

(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-(1',1'-dimethyl-2'-hydroxyethyl)-1,3-dioxane + benzaldehyde (100-52-7) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + (2S*,4S*)-5,5-dimethyl-4-hydroxy-2-phenyl-1,3-dioxane + (2S*,4R*)-5,5-dimethyl-4-hydroxy-2-phenyl-1,3-dioxane

Conditions	Yield
With triethylamine at 0 - 65℃; for 6h; Inert atmosphere; Reflux; Optical yield = 16 %de; diastereoselective reaction;	A 51 %Spectr. B n/a C n/a

(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-(1',1'-dimethyl-2'-hydroxyethyl)-1,3-dioxane → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With triethylamine; crotonaldehyde at 0 - 65℃; for 6h; Inert atmosphere; Reflux;	62 %Spectr.

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2-methyl-propan-1-ol (78-83-1)

Conditions	Yield
With tri-n-propylamine

methanol (67-56-1) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Conditions	Yield
With formaldehyd; triethylamine at 40 - 94℃;

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 2-(5-butyl-5-ethyl[1,3]dioxane-2-yl)-2-methylpropane-1-ol

Conditions	Yield
With nafion NR-50 In benzene Dean-Stark;	99%

sodium cyanide (773837-37-9) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → pantolactone (79-50-5)

Conditions	Yield
With sulfuric acid for 3h; pH=9.5; Reflux;	98.9%
With sulfuric acid In water at 100℃; for 1h;	86.9%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 1,2,3,4-tetrahydronaphthalen-2-one (530-93-8) → 2,3-dihydro-2,2-dimethyl-1H-benzo[f]chromene (1011489-51-2)

Conditions	Yield
With hydrogenchloride In formic acid at 5 - 10℃; for 1h;	96.4%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + β-naphthol (135-19-3) → 3,3-dimethyl-4-(2-hydroxy-1-naphthyl)benzo[f]chroman

Conditions	Yield
With hydrogenchloride; acetic acid at 50 - 60℃; for 4h;	95%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + hydrogen cyanide (74-90-8) → pantolactone (79-50-5)

Conditions	Yield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; hydrogen cyanide In water at 0 - 10℃; for 0.25h; Stage #2: With sulfuric acid for 1h; Reflux;	93.1%
Verseifung des Reaktionsprodukts mit Salzsaeure;

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 3-Hydroxy-2,2-dimethylpropanoic acid (4835-90-9)

Conditions	Yield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde With sodium hydroxide at 85 - 95℃; for 2h; Stage #2: With ammonium hydroxide; H1044 at 60℃; for 8h; pH=7 - 9;	91%
With phosphotungstic acid; dihydrogen peroxide In water at 55℃; for 2h; Temperature; Reagent/catalyst; Time;	85%
With sodium hydroxide; oxygen; palladium/alumina at 39.85℃; under 760 Torr; Kinetics; Further Variations:; Temperatures;
Multi-step reaction with 2 steps 1: water; aluminium amalgam 2: potassium permanganate View Scheme

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran	90%
With aluminium amalgam; water
With sodium amalgam; water

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + Pentaerythritol (115-77-5) → 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1)

Conditions	Yield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; Pentaerythritol; sulfuric acid In water; xylene at 60℃; for 14h; Stage #2: With sodium hydroxide Conversion of starting material;	89%
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; Pentaerythritol; hydrogenchloride In water at 70℃; for 8h; Stage #2: With sodium hydroxide at 40℃; pH=6.5; Conversion of starting material;	83%
sulfuric acid In water at 60℃; for 6h; Conversion of starting material;	80%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → 2-(4',4',5',5'-tetramethylimidazolidine-2'-yl)-2-methylpropanol (1309974-80-8)

Conditions	Yield
In chloroform for 24h; Molecular sieve; Reflux;	87%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + methyl 2-(bromomethyl)propenoate (4224-69-5) → 4,6-Dihydroxy-5,5-dimethyl-2-methylene-hexanoic acid methyl ester (138832-37-8)

Conditions	Yield
With indium In water for 5h; Ambient temperature;	85%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + allyl bromide (106-95-6) → 2,2-dimethyl-5-hexen-1,3-diol (138832-34-5)

Conditions	Yield
With indium In water for 3h; Ambient temperature;	85%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) → trans-2-(5-ethyl-5-hydroxymethyl-1,3-dioxane-2-yl)-2-methylpropane-1-ol

Conditions	Yield
hydrogenchloride In water at 60℃; for 5h; Product distribution / selectivity;	84%
toluene-4-sulfonic acid In water at 55 - 70℃; for 1 - 3h; pH=1.3; Product distribution / selectivity;	30%
hydrogenchloride In water at 60℃; for 5h; Product distribution / selectivity;

3-phenyl-propionaldehyde (104-53-0) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + isocyanoacetic acid methyl ester (39687-95-1) → C18H25N5O3

Conditions	Yield
Stage #1: 3-phenyl-propionaldehyde; 2,2-dimethyl-3-hydroxypropionaldehyde With ammonium hydroxide In toluene for 2h; Sonication; Stage #2: isocyanoacetic acid methyl ester With trimethylsilylazide In toluene Sonication; diastereoselective reaction;	83%

3,4-dihydro-2H-pyran (110-87-2) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 2,2-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-propanal (52113-84-5)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; Addition;	80%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → (E)-4-Methoxy-2,2-dimethyl-but-3-en-1-ol

Conditions	Yield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In diethyl ether for 1.5h; Metallation; Stage #2: 2,2-dimethyl-3-hydroxypropionaldehyde In diethyl ether at 20℃; for 10h; olefination;	80%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl trans-4,4-dimethyl-5-hydroxypent-2-enoate (158045-09-1)

Conditions	Yield
In benzene at 80℃;	78%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → pivalaldehyde (630-19-3)

Conditions	Yield
With triethyl borane; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane a) -30 deg C, 30 min, b) room temperature, 6 h;	74%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + malononitrile (109-77-3) → 6-amino-3,3-dimethyl-2,4-dihydropyran-5-carbonitrile (337310-91-5)

Conditions	Yield
With sodium tetrahydroborate In isopropyl alcohol at 0 - 20℃; for 4h;	74%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,7-Dihydroxynaphthalene (582-17-2) → 1,12-dihydroxy-14-(2-hydroxymethylprop-2-yl)-14H-dibenzo[a,j]xanthene

Conditions	Yield
With hydrogenchloride; acetic acid at 50 - 60℃; for 4h;	72%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 3-hydroxy-2,2-dimethylpropionaldoxime (36559-87-2)

Conditions	Yield
With hydroxylamine hydrochloride; water; potassium carbonate In ethanol at 70℃; for 48h; Cooling with ice;	71%
With hydroxylamine
With hydroxylamine hydrochloride

1.3-propanedithiol (109-80-8) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane (219606-56-1)

Conditions	Yield
With boron trifluoride diethyl etherate thioacetalization;	70%
With boron trifluoride diethyl etherate at 20℃;

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → C5H11(2)HO2 (344948-08-9)

Conditions	Yield
With lithium aluminium deuteride In tetrahydrofuran at 65℃; for 1.5h;	70%

methanol (67-56-1) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → Methyl 2,2-dimethyl-3-hydroxypropionate (14002-80-3)

Conditions	Yield
With sodium methylate; potassium iodide at 17℃; electrooxidation;	68%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + aniline (62-53-3) → N-phenyl-2-(hydroxymethyl)-2-methylpropylamine (94844-02-7)

Conditions	Yield
With sodium cyanoborohydride; zinc(II) chloride In methanol for 36h; Ambient temperature;	66%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + N-cyclohexyl-hydroxylamine (2211-64-5) → 3-(cyclohexylimino)-2,2-dimethylpropanol N-oxide

Conditions	Yield
In benzene for 5h; Heating;	66%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + trimethyl orthoformate (149-73-5) → 3-Hydroxy-2,2-dimethylpropanal dimethyl acetal (87395-22-0)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 24h;	66%

Upstream product

• 50-00-0 formaldehyd 
• 78-84-2 isobutyraldehyde 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 7647-01-0 hydrogenchloride 
• 59676-94-7 bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine 
• 7664-93-9 sulfuric acid 
• 111-42-2 2,2'-iminobis[ethanol] 
• 590-86-3 isovaleraldehyde 
• 100-52-7 benzaldehyde 
• 558-30-5 2-methyl-1,2-epoxypropane 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 219606-56-1 2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane 
• 15833-82-6 3-hydroxy-4,4-dimethyltetrahydrofuran 

Downstream Products

• 1115-20-4 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate 
• 76-35-7 2,2-dimethyl-1,3-butanediol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 131762-47-5 4-hydroxy-3,3-dimethyl-2-p-toluidino-butyronitrile 
• 101264-42-0 2-benzylamino-4-hydroxy-3,3-dimethyl-butyronitrile 
• 806615-33-8 3-benzylamino-4,4-dimethyl-dihydro-furan-2-one 
• 10232-92-5 (R,S)-2,4-Dihydroxy-3,3-dimethylbutyronitrile 
• 74793-10-5 3,5,5-Trimethyl-5,6-dihydro-2H-pyran-2-on 
• 19295-57-9 3-hydroxy-2,2-dimethylpropionitrile 
• 630-19-3 pivalaldehyde 
• 4835-90-9 3-Hydroxy-2,2-dimethylpropanoic acid 
• 1455-42-1 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane 
• 21491-96-3 methyl 3-chloro-2,2-dimethylpropionate 
• 334874-91-8 2-methyl-2-(8-nitro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl)-propan-1-ol 

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Two novel epoxide monomers 3,3-dimethoxy-propanyl glycidyl ether (DMPGE) and 3,3-dimethoxy-2,2-dimethylpropanyl glycidyl ether (DDPGE) were developed for the introduction of multiple aldehyde functionalities into the poly(ethylene glycol) (PEG) backbone. The acetal protecting group for the aldehyde functionality is stable against the harsh, basic conditions of the anionic ring-opening polymerization. Both monomers could be homopolymerized as well as copolymerized randomly with ethylene oxide (EO) in a controlled fashion. Copolymers with molecular weights (Mn) in the range of 4500-20100 g/mol and low dispersity (Mw/Mn) between 1.06 and 1.14 were obtained. The polymers were characterized by size exclusion chromatography, 1H NMR spectroscopy, and by differential scanning calorimetry regarding their thermal properties. The controlled character of the copolymerization was verified by MALDI-TOF. To study the distribution of the acetal-protected aldehyde functionalities at the polyether chains, the copolymerization with EO was monitored by in situ 1H NMR kinetics experiments for both monomers. These measurements revealed almost ideally random distribution of the comonomers with reactivity ratio pairs rEO = 0.96, rDMPGE = 1.04 and rEO = 1.20, rDDPGE = 0.83. The acetal functionalities of DMPGE polymers were successfully addressed by hydrazone formation. In addition, DDPGE copolymers were successfully deprotected in acidic media, and various transformations yielded aldehyde-, ester-, and nitrile-functionalized PEG while maintaining a dispersity below 1.1. Consequently, these monomers represent promising building blocks for the synthesis of multifunctional PEG for a variety of biomedical purposes.

Preparation method of hydroxypivalaldehyde and application of hydroxypivalaldehyde in preparation of neopentyl glycol

The invention provides a preparation method of 2,2-dimethyl-3-hydroxypropanal and application thereof in preparation of neopentyl glycol. The 2,2-dimethyl-3-hydroxypropanal is prepared from an epoxy compound by a hydroformylation method. The method has the advantages of good atom economy, low raw material cost, no wastewater generation, and high yield. The invention also provides the application of the 2,2-dimethyl-3-hydroxypropanal in preparation of the neopentyl glycol. The application method circumvents the disadvantages of the conventional methods in the prior art, the reaction system is simple, and the industrial application prospect is excellent.

Preparation method of hydroxyaldehyde and method for resolving optical isomer by using electrodialysis technology

The present invention provides a process for preparing hydroxyaldehydes using an immobilized catalyst, wherein the immobilized catalyst comprises a solid support and a tertiary amine-based functionalgroup. The invention also provides a method for preparing a polyhydroxy alcohol compound and a polyhydroxy acid compound. The invention further provides a method for splitting the optical isomer fromthe raceme through electrodialysis.