2-(Benzo[d][1,3]dioxol-5-yl)ethanol Chemical Properties

Boiling point:

115-117

Density 

1.269±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

14.87±0.10(Predicted)

Appearance

Light yellow to yellow Liquid

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

HazardClass 

IRRITANT

2-(Benzo[d][1,3]dioxol-5-yl)ethanol Usage And Synthesis

Synthesis

6.2.1 Synthesis of 2-(1,3-benzodioxol-5-yl)ethanol (21) [9]. A solution of anhydrous THF (10 mL) with acid 20 (3.00 mmol) was slowly added dropwise to a suspension of anhydrous THF (20 mL) with lithium aluminum hydride (0.114 g, 3.00 mmol) over 15 min. After 4 h of reaction, methanol (1 mL) and 10% NaOH aqueous solution (2 mL) were added sequentially to quench the excess reducing agent until aluminum hydroxide precipitate was formed. Subsequently, the reaction mixture was neutralized with 10% aqueous hydrochloric acid solution (about 5 mL). The resulting mixture was extracted with ethyl acetate (3 x 15 mL), and the combined organic phases were washed with brine, concentrated under reduced pressure, and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (eluent: CHCl3/EtOH = 100:1) to afford the target product, sterol 21, as a yellow oil in a yield of 0.489 g (98%). Thin layer chromatography (TLC) Rf = 0.5 (CHCl3/EtOH = 20:1). IR (thin film, cm-1): 3351, 2883, 1607, 1503, 1489, 1442, 1247, 1040. 1H NMR (CDCl3): δ 1.87 (br, 1H, ArCH2CH2OH); 2.76 (t, J = 6.5 Hz, 2H, ArCH2CH2OH); 3.78 (t, J = 6.5 Hz, 2H, ArCH2CH2OH); 5.91 (s, 2H, OCH2O); 6.65 (dd, J = 7.8 Hz, J = 1.6 Hz, 1H, 4'); 6.71-6.70 (m, 1H, 2'); 6.75 (d, J = 7.8 Hz, 1H, 5').13C NMR (CDCl3): δ 38.6 (ArCH2CH2OH); 63.5 (ArCH2CH2OH); 100.6 (OCH2O); 108.1 (CH, 2'); 109.1 (CH, 5'); 121.7 (CH, 6'); 132.0 (C, 1'); 145.9 (CH, 4'); 147.5 (CH, 3').

References

[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3333 - 3340
[2] Patent: US6342610, 2002, B2. Location in patent: Page column 121
[3] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 601 - 610
[4] Tetrahedron Letters, 1997, vol. 38, # 25, p. 4347 - 4350
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4618 - 4627

2-(Benzo[d][1,3]dioxol-5-yl)ethanol(6006-82-2)Related Product Information

• NOSCAPINE HYDROCHLORIDE
• (+)-Bicuculline
• (+)-B-HYDRASTINE HCL
• CEPHALOTAXINE
• RHOEADINE
• CHELIDONINE
• 1,3-BENZODIOXOLE-5-GLYCOLIC ACID
• Narcotine
• HARRINGTONINE
• (-)-BICUCULLINE METHOBROMIDE
• 3,4-(METHYLENEDIOXY)PHENYLACETIC ACID
• Phenethyl alcohol
• PIPEROIN
• pisatin
• (-)-BICUCULLINE METHIODIDE
• (-)-BICUCULLINE METHOCHLORIDE
• (-)-BICUCULLINE METHCHLORIDE, 1(S),9(R)
• OXYCHELIDONINE