5-BENZYLOXY-1-PENTANOL

5-BENZYLOXY-1-PENTANOL Property

Boiling point:

140 °C/0.4 mmHg (lit.)

Density 

1.008 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.505(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

pka

15.15±0.10(Predicted)

Specific Gravity

1.008

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C12H18O2/c13-9-5-2-6-10-14-11-12-7-3-1-4-8-12/h1,3-4,7-8,13H,2,5-6,9-11H2

InChIKey

RZVDPWSEPVHOPU-UHFFFAOYSA-N

SMILES

C(O)CCCCOCC1=CC=CC=C1

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2909498090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-BENZYLOXY-1-PENTANOL Chemical Properties,Usage,Production

Uses

5-Benzyloxy-1-pentanol (5-(benzyloxy)pentan-1-ol) may be used as a starting material in the synthesis of 5-benzyloxypentanal and (±)tanikolide.

General Description

5-Benzyloxy-1-pentanol (5-(benzyloxy)pentan-1-ol) has been synthesized by reacting pentane-1,5-diol with benzyl chloride. Its enthalpy of vaporization at boiling point has been determined.

Synthesis

To a stirred suspension of a 60% sodium hydride (NaH) dispersion in mineral oil (2.30 g, 57.69 mmol), an anhydrous N,N-dimethylformamide (DMF, 150 mL) solution of 1,5-pentanediol (5.0 g, 48.07 mmol) was slowly added dropwise at 0°C over 15 minutes. After dropwise addition, the reaction mixture was stirred at room temperature for 1 hour. Subsequently, benzyl bromide (5.75 mL, 48.07 mmol) was slowly added over 15 minutes and stirring was continued at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was quenched with ice-cold water. The crude product was extracted with ethyl acetate (2 x 30 mL), the organic layers were combined, washed with saturated brine (3 times), dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether-ethyl acetate (7:3, v/v) as eluent to obtain the target product 5-benzyloxy-1-pentanol. Yield: 89% (7.87 g) as a colorless oily liquid. IR spectrum (CHCl3, cm-1): υmax 700, 714, 1028, 1072, 1116, 1177, 1278, 1316, 1388, 1453, 2865, 2938, 3064, 3332; 1H NMR (200 MHz, CDCl3): δ 1.47-1.70 (m, 6H), 3.47 (t, J = 6.3 Hz, 2H), 3.62 (t, J = 6.1 Hz, 2H), 4.49 (s, 2H), 7.31 (s, 5H); 13C NMR (50 MHz, CDCl3): δ 22.3, 29.3, 32.3, 62.2, 70.2, 72.8, 127.5, 128.2, 138.3; High-resolution Mass Spectrometry (ESI): calculated value [C12H18O2 + H]+ (M + H) 195.1385, measured value 195.1390.

References

[1] Journal of the American Chemical Society, 2007, vol. 129, # 5, p. 1465 - 1469
[2] Organic Letters, 2016, vol. 18, # 7, p. 1622 - 1625
[3] Journal of the American Chemical Society, 2015, vol. 137, # 1, p. 420 - 424
[4] Tetrahedron Letters, 2016, vol. 57, # 1, p. 25 - 28
[5] Helvetica Chimica Acta, 2015, vol. 98, # 10, p. 1395 - 1402