10210-17-0

Basic information

• Product Name: 3-(4-HYDROXYPHENYL)-1-PROPANOL
• Synonyms: 4-(3-HYDROXY-PROPYL)-PHENOL;3-(4-HYDROXYPHENYL)-1-PROPANOL;3-(4-hydroxyphenyl)propan-1-ol;4-Hydroxybenzene-1-propanol;4-Hydroxyhydrocinnamyl alcohol;Ai3-12108;Benzenepropanol, 4-hydroxy-;Einecs 233-511-4
• CAS NO: 10210-17-0
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 233-511-4
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 10210-17-0.mol
• Article Data: 40

Chemical Properties

• Melting Point: 51-54 °C(lit.)
• Boiling Point: 311.6 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.129 g/cm³
• Vapor Pressure: 0.000239mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.05±0.15(Predicted)
• CAS DataBase Reference: 3-(4-HYDROXYPHENYL)-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-HYDROXYPHENYL)-1-PROPANOL(10210-17-0)
• EPA Substance Registry System: 3-(4-HYDROXYPHENYL)-1-PROPANOL(10210-17-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 10210-17-0(Hazardous Substances Data)

Usage

Uses

3-(4-Hydroxyphenyl)-1-propanol was used in the synthesis of (?)-centrolobine.

InChI:InChI=1/C9H12O2/c10-7-1-2-8-3-5-9(11)6-4-8/h3-6,10-11H,1-2,7H2

Synthetic route

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Stage #1: 3-(4-hydroxyphenyl)propionic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 - 5h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran; ethyl acetate	100%
Stage #1: 3-(4-hydroxyphenyl)propionic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 - 5h; Heating / reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water; ethyl acetate at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate pH=7.0;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 - 5h; Heating / reflux;	100%

4-hydroxyphenylpropionic acid (501-97-3) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With borane-THF; Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;	99%
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h;	98%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;	98%

para-coumaryl alcohol (3690-05-9) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12h;	98%

methyl 3-(4-acetyloxyphenyl)propanoate (54965-55-8) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With lithium borohydride In tetrahydrofuran at 70℃; for 22h;	95.5%
With lithium aluminium tetrahydride; diethyl ether

3-(4-hydroxy-phenyl)-propionic acid ethyl ester (23795-02-0) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	95%
Stage #1: 3-(4-hydroxy-phenyl)-propionic acid ethyl ester With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Heating / reflux; Stage #2: With ethyl acetate; sodium sulfate In tetrahydrofuran; water Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=7.0;	68%
With lithium aluminium tetrahydride In tetrahydrofuran at 55℃; for 12h;	13.5 g
Multi-step reaction with 3 steps 1: 89.1 percent / K2CO3; NaI / acetone / 48 h / Heating 2: 66.2 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 84.3 percent / H2 / 10 percent Pd/C / ethanol / 20 °C / 760 Torr View Scheme

3-(4-acetoxyphenyl)propyl acetate (25823-43-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With aluminum oxide In neat (no solvent) at 65℃; for 0.0416667h; microwave irradiation;	92%

3-[4-(benzyloxy)phenyl]propan-1-ol (61440-45-7) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid	89%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr; Hydrogenolysis;	84.3%
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;	0.149 g

p-Coumaric Acid (7400-08-0) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With whole cell cultures of dichomitus albidofuscus at 24℃; for 72h; Darkness; Microbiological reaction;	82%
Multi-step reaction with 3 steps 1: aq. HCl / 6 h / Heating 2: H2 / 10percent Pd/C / methanol / 0.5 h / 760 Torr / Ambient temperature 3: LiBH4 / diethyl ether; toluene / 0.25 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: pyridine / 1 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / 1,4-dioxane / 1 h / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: potassium hydroxide / ethanol / 8 h / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 2250.23 Torr View Scheme

bis(t-butyldimethylsilyl)-3-(4-hydroxyphenyl)propanol → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
aluminum oxide for 0.183333h; Irradiation;	78%
With cerium(IV) triflate In acetonitrile at 20℃; for 0.25h;	75%

4-(3-hydroxypropyl)-2,6-di-tert-butylphenol (36294-23-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
at 324℃; for 11h;	76%

4-(3-hydroxypropyl)-2,6-di-tert-butylphenol (36294-23-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 2-tert-butyl-4-(3-hydroxypropyl)phenol (95970-34-6)

Conditions	Yield
at 280 - 300℃; for 24h; Inert atmosphere;	A 57% B 9%

4-hydroxyphenylpropionic acid (501-97-3) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 4-(3-hydroxypropyl)cyclohex-3-enol (1379072-68-0)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	A 48% B 23%

(E)-4-(3-hydroxyprop-1-enyl)phenol (20649-40-5) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; under 2250.23 Torr; for 6h;	48%

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 4-hydroxyphenylpropionic acid (501-97-3) + recorcinol (108-46-3)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In water at 100℃; Product distribution;	A 22% B 8% C 38%

acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester (42385-89-7) → 3,5-dihydroxyphenol (108-73-6) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 2-(3-(4-hydroxyphenyl)propyl)benzene-1,3,5-triol (127265-09-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol Product distribution;	A 7.5% B 6% C 6%

3-(p-methoxyphenyl)-1-propanol (5406-18-8) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With hydrogen bromide; acetic acid

3-(4-hydroxyphenyl)propanoic acid amide (23838-70-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With ethanol; sodium

4-(3-chloropropyl)phenol (99103-80-7) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With sodium acetate; acetic acid Erwaermen des Reaktionsprodukts mit Alkalilauge;

19--ent-kauran-17-al → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + C20H34O2

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	A 2 mg B 5 mg

dehydrocuspidiol (51318-05-9) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With zinc In acetic acid for 1h; Heating;	0.004 g

1,3-Dicyclohexyl-2-[3-(4-hydroxy-phenyl)-propionyl]-isourea → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
With lithium borohydride In tetrahydrofuran for 16h; Yield given;

3-(4'-acetoxyphenyl)propionic acid (7249-16-3) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / K2CO3 / dimethylformamide / 23 h / 20 °C 2: 95.5 percent / LiBH4 / tetrahydrofuran / 22 h / 70 °C View Scheme

ethyl 3-(4-(benzyloxy)phenyl)propanoate (186895-45-4) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66.2 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 84.3 percent / H2 / 10 percent Pd/C / ethanol / 20 °C / 760 Torr View Scheme

4-hydroxyphenylpropionic acid (501-97-3) + sodium hydroxide → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 6 h / Ambient temperature 2: LiBH4 / tetrahydrofuran / 16 h View Scheme

4-benzyloxybenzyl alcohol (836-43-1) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 7 steps 1: 2.840 g / thionyl chloride / benzene; pyridine / 1 h / Ambient temperature 2: 0.603 g / NaH / paraffin; dimethylformamide / 3 h / Ambient temperature 3: 0.370 g / KON / ethanol; H2O / 3 h / Heating 4: 0.249 g / 150 - 160 °C / 15 - 20 Torr 5: 1.663 g / diethyl ether / 2 h / Ambient temperature 6: 1.305 g / LiAlH4 / diethyl ether; tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h 7: 0.149 g / H2 / 10percent Pd-charcoal / ethanol / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: 2.840 g / thionyl chloride / benzene; pyridine / 1 h / Ambient temperature 2: diethyl malonate / paraffin; dimethylformamide / 3 h / Ambient temperature 3: 0.370 g / KON / ethanol; H2O / 3 h / Heating 4: 0.249 g / 150 - 160 °C / 15 - 20 Torr 5: 1.663 g / diethyl ether / 2 h / Ambient temperature 6: 1.305 g / LiAlH4 / diethyl ether; tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h 7: 0.149 g / H2 / 10percent Pd-charcoal / ethanol / Ambient temperature View Scheme

4-[4-(3-hydroxy-propyl)-phenoxy]-2-methyl-but-2-en-1-ol (51593-96-5) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.088 g / manganese dioxide / CHCl3 / 4 h / Ambient temperature 2: 0.004 g / Zn / acetic acid / 1 h / Heating View Scheme

methyl (E)--2-methylcrotonate (51318-06-0) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.077 g / LiAlH4 / tetrahydrofuran; diethyl ether / 1.) room temperature, 1h, 2.) reflux, 2 h 2: 0.088 g / manganese dioxide / CHCl3 / 4 h / Ambient temperature 3: 0.004 g / Zn / acetic acid / 1 h / Heating View Scheme

methyl 3-(4-benzyloxyphenyl)propanoate (24807-40-7) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.305 g / LiAlH4 / diethyl ether; tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h 2: 0.149 g / H2 / 10percent Pd-charcoal / ethanol / Ambient temperature View Scheme

3-(4-benzyloxyphenyl)propanoic acid (50463-48-4) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.663 g / diethyl ether / 2 h / Ambient temperature 2: 1.305 g / LiAlH4 / diethyl ether; tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h 3: 0.149 g / H2 / 10percent Pd-charcoal / ethanol / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 85 percent / lithium aluminium hydride / diethyl ether / 2.5 h / Heating 2: 89 percent / hydrogen / 10percent palladium-carbon / acetic acid View Scheme

ortho-nitrophenyl selenocyanate (51694-22-5) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 4-[3-(2-Nitro-phenylselanyl)-propyl]-phenol (95081-49-5)

Conditions	Yield
With tributylphosphine In tetrahydrofuran for 5h; Ambient temperature;	100%

2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 2-{3-[4-(3-hydroxy-propyl)-phenoxy]-propyl}-isoindole-1,3-dione (205318-86-1)

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	100%
With potassium carbonate In acetone for 24h; Heating;	73%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + carbonic acid dimethyl ester (616-38-6) → 3-(4-hydroxyphenyl)propyl methyl carbonate (1390633-75-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene Reflux;	100%
With zeolite NaY at 90℃; for 240h; Reagent/catalyst;

2-(2,6-dimethyl-4-tritylphenoxy)ethyl toluene-4-sulfonate (881890-56-8) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 3-{4-[2-(2,6-dimethyl-4-tritylphenoxy)ethoxy]phenyl}propan-1-ol (881890-57-9)

Conditions	Yield
With sodium ethanolate In acetonitrile for 6h; Heating;	99%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 2,6-dibromo-4-(3-hydroxypropyl)phenol (38972-02-0)

Conditions	Yield
With bromine In acetic acid at 20℃;	99%
With bromine; acetic acid at 20℃;

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + methanesulfonyl chloride (124-63-0) → dimesylate of p-hydroxydihydrocinnamyl alcohol (251978-03-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	98%
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	61%
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	61%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + chloroformic acid ethyl ester (541-41-3) → carbonic acid ethyl ester 4-(3-hydroxy-propyl)-phenyl ester

Conditions	Yield
With triethylamine In acetonitrile at -80 - 20℃; Inert atmosphere;	98%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate (990-91-0) → 3-[4-(dibenzyl)phosphoryloxy]phenyl-1-propanol

Conditions	Yield
With tetrahexylammonium iodide; silver(l) oxide In dichloromethane at 20℃; for 20h;	97%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 4-(3-bromopropyl)phenol (52273-55-9)

Conditions	Yield
With hydrogen bromide at 80℃; for 20h;	96%
With carbon tetrabromide; triphenylphosphine In dichloromethane Appel reaction; Cooling with ice;	95%
With hydrogen bromide In water at 80℃; for 20h;	92%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + MeO-(CH2CH2O)n-CH2CH2-OSO2CH3 → MeO-(CH2CH2O)nCH2CH2-O-p-C6H4(CH2)3OH, n = ca. 110

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 40h;	96%

3-iodopyridine (1120-90-7) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 3-(4-(pyridin-3-yloxy)phenyl)propan-1-ol

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 21h; Inert atmosphere; chemoselective reaction;	96%

vinyl acetate (108-05-4) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → C10H12O4

Conditions	Yield
With rubidium fluoride In acetonitrile at 80℃; for 0.5h;	96%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + benzyl chloride (100-44-7) → 3-[4-(benzyloxy)phenyl]propan-1-ol (61440-45-7)

Conditions	Yield
With potassium carbonate In ethanol for 6h; Inert atmosphere; Reflux;	95%
With potassium carbonate In ethanol for 3h; Heating;	94%
With sodium hydride 1.) DMF, 50 deg C 2.) 50 deg C; Yield given. Multistep reaction;

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + benzyl bromide (100-39-0) → 3-[4-(benzyloxy)phenyl]propan-1-ol (61440-45-7)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 12h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	92%
With sodium hydride In N,N-dimethyl-formamide for 12h; Heating;	90%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + (2-methylallyl)tertiobutyl-dimethylsilane (143422-89-3) → 3-(4-((tert-butyl(dimethyl)silyl)oxy)phenyl)propan-1-ol (215776-67-3)

Conditions	Yield
Stage #1: 3-(4-hydroxyphenyl)propan-1-ol; (2-methylallyl)tertiobutyl-dimethylsilane With scandium tris(trifluoromethanesulfonate) In various solvent(s) at 20℃; for 4h; Stage #2: With water In various solvent(s) at 20℃; for 3h;	95%

di-tert-butyl dicarbonate (24424-99-5) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 3-(4-t-butoxycarbonyl)phenyl-1-propanol (1559067-01-4)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	95%
With 18-crown-6 ether; potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	95%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + methyl iodide (74-88-4) → 3-(p-methoxyphenyl)-1-propanol (5406-18-8)

Conditions	Yield
With potassium carbonate In acetone	94.9%
With potassium carbonate In diethyl ether; acetone	94.93%

vinyl laurate (2146-71-6) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 3-(4-hydroxyphenyl)propyl dodecanoate (1390633-84-7)

Conditions	Yield
With lipase B from Candida sp. expressed in Aspergillus niger In aq. buffer for 20h; pH=7.2; Green chemistry; Enzymatic reaction;	94.1%
With Candida antarctica lipase B in agarose gel droplets Pickering-stabilized by UiO-66/Fe3O4 nanoparticles In acetone at 20℃; for 12h; Reagent/catalyst; Enzymatic reaction;

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + (4,6-dichloro-[1,3,5]triazin-2-yloxymethylene)-dimethyl-ammonium; fluoride → 4,6-dichloro-2-hydroxy-1,3,5-triazine (15791-08-9) + formic acid 3-(4-hydroxyphenyl)propyl ester

Conditions	Yield
In dichloromethane at 25℃; for 0.25h;	A n/a B 94%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 4-(3-iodopropyl)phenol (179548-39-1)

Conditions	Yield
With hydrogen iodide at 100℃;	94%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 5h;	32%
With hydrogen iodide

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + tert-butylchlorodiphenylsilane (58479-61-1) → 3-(4-hydroxyphenyl)-1-(tert-butyldiphenylsilyloxy)propane (400838-08-6)

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	94%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 2,2,2-trichloroacetophenone (2902-69-4) → 4-hydroxy-benzenepropanol-α-benzoate

Conditions	Yield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine In acetonitrile at 20 - 25℃; for 12h;	94%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 4-Phenylbutyric acid (1821-12-1) → 4-phenyl-butyric acid 4-(3-hydroxy-propyl)-phenyl ester + 3-(p-hydroxyphenyl)propyl 4-phenylbutyrate + 4-phenyl-butyric acid 4-[3-(4-phenyl-butyryloxy)-propyl]-phenyl ester

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 6h; Heating;	A n/a B 93% C n/a

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + prenyl bromide (870-63-3) → 3-methyl-2-butenyl 3-[4-(3-methyl-2-butenyloxy)-phenyl]propyl ether (410087-93-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	93%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 4-Phenylbutyric acid (1821-12-1) → 3-(p-hydroxyphenyl)propyl 4-phenylbutyrate

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 6h; Heating;	93%

Upstream product

• 99103-80-7 4-(3-chloropropyl)phenol 
• 27542-85-4 4-acetoxycinnamic acid 
• 20649-40-5 (E)-4-(3-hydroxyprop-1-enyl)phenol 
• 3690-05-9 4-hydroxycinnamic alcohol 
• 2979-06-8 ethyl (E)-4-hydroxycinnamate 
• 22214-30-8 4-(4'-hydroxyphenyl)but-3-en-2-one 
• 1397255-02-5 ethyl 3-(4-(2-(4-hydroxy-3-methoxyphenyl)-2-oxoethoxy)phenyl)acrylate 
• 1397255-01-4 3-(4-(2-(4-hydroxy-3-methoxyphenyl)-2-oxoethoxy)phenyl)acrylaldehyde 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 36294-23-2 4-(3-hydroxypropyl)-2,6-di-tert-butylphenol 
• 75869-54-4 Irganox-1010 
• 55226-78-3 methyl (2E)-3-[4-(acetyloxy)phenyl]-2-propenoate 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 3943-97-3 methyl 4-hydroxycinnamate 

Downstream Products

• 80373-18-8 3-(4'-hydroxyphenyl)-1-propyl acetate 
• 61440-45-7 3-[4-(benzyloxy)phenyl]propan-1-ol 
• 881890-57-9 3-{4-[2-(2,6-dimethyl-4-tritylphenoxy)ethoxy]phenyl}propan-1-ol 
• 952315-71-8 6-(4-hydroxyphenyl)-(3E)-hexen-2-one 
• 74882-16-9 3-(4-(methoxymethoxy)phenyl)propanal 
• 201534-35-2 1-Methoxymethoxy-4-(4-methyl-pent-3-enyl)-benzene 
• 51593-96-5 4-[4-(3-hydroxy-propyl)-phenoxy]-2-methyl-but-2-en-1-ol 
• 51318-04-8 diacetylcuspidiol 
• 51318-05-9 dehydrocuspidiol 
• 90562-26-8 3-(4-chlorophenyl)-1-iodopropane 
• 1112406-70-8 2-(2-(2-(4-(3-hydroxypropyl)phenoxy)ethoxy)ethoxy)ethyl tosylate 
• 179548-39-1 4-(3-iodopropyl)phenol 
• 764687-71-0 3-[4-(2-{2-[2-(4-cyclohepta-2,4,6-trienyl-phenoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-propan-1-ol 
• 25823-43-2 3-(4-acetoxyphenyl)propyl acetate 

Relevant articles and documents

Cuspidiol: a new monomeric phenyl propanoid

-

A convenient method to reduce hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3

The reduction of hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3 is described. Borane is generated by the reaction of NaBH4 with Me2SO4 in THF, which is as efficient as the commercial one. B(OMe)3 has been successfully applied to increase the reactivity and selectivity of this reaction. The optimum ratio of borane/B(OMe)3/acid is studied, and a variety of hydroxyl-substituted aromatic acids are reduced in good yields.

Synthesis and antiproliferative activity of a new compound containing an α-methylene-γ-lactone group

The biological activity of compound 9 obtained by introducing an α-methylene-γ-butyrolactone group into 3-(4-hydroxyphenyl)propionic acid, 1, was studied for possible effects on HL-60 cells, murine splenocytes, and human peripheral mononuclear cells (PBMC). 9 induced apoptosis in the HL-60 cell line and has a clear capacity to inhibit proliferation induced in murine splenocytes and PBMC by different mitogenic agents with no apparent toxic side effects. 9 was synthesized from 1, and its structure and stereochemistry were elucidated by spectroscopic methods.

DITERPENES FROM BACCHARIS SPECIES

The investigation of ten Baccharis species afforded in addition to known compounds eight new diterpenes, four ent-labdanes, three kaurenes and a clerodane derivative.Furthermore, two new p-hydroxyacetophenones, a flavone, 3'-methoxyxanthomicrol and two matricaria ester derivatives were isolated.The structures were elucidated by spectroscopic methods and a few chemical transformations.The chemotaxonomic situation of the large genus is discussed briefly. - Keywords: Baccharis species; Compositae; diterpenes; ent-labdanes; clerodane; ent-kauranes; p-hydroxyacetophenone derivatives; acetylenes; flavone; 3'-methoxyxanthomicrol.

-

-

Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi

The reductive activity of various basidiomycetous fungi towards carbonyl compounds was screened on an analytical level. Some strains displayed high reductive activities toward aromatic carbonyls and aliphatic ketones. Utilizing growing whole-cell cultures of Dichomitus albidofuscus, the reactions were up-scaled to a preparative level in an aqueous system. The reactions showed excellent selectivities and gave the respective alcohols in high yields. Carboxylic acids were also reduced to aldehydes and alcohols under the same conditions. In particular, benzoic, vanillic, ferulic, and p-coumaric acid were reduced to benzyl alcohol, vanillin, dihydroconiferyl alcohol and 1-hydroxy-3-(4-hydroxyphenyl)propan, respectively.

CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE

The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.