2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL Chemical Properties

Boiling point:

226℃

Density 

0.981

Flash point:

95℃

storage temp. 

2-8°C

pka

15.06±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-21/22-36/37/38-41-37/38

Safety Statements 

16-23-26-36/37/39-39

RIDADR 

UN1987

HS Code 

2932990090

2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL Usage And Synthesis

Uses

2-(Tetrahydropyran-4-yl)-ethanol is mainly used as an intermediate in organic synthesis, especially in the field of pharmaceutical manufacturing.

Synthesis

General procedure for the synthesis of tetrahydropyran-4-ethanol from ethyl tetrahydropyran-4-yl-acetate: To a stirred suspension of lithium aluminium hydride (5.10 g, 138 mmol) in tetrahydrofuran (200 mL) at 0 °C, a tetrahydrofuran (50 mL) solution of ethyl 2-(tetrahydropyran-4-yl)acetate (22.0 g, 138 mmol) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was heated to reflux overnight. Upon completion of the reaction, the mixture was cooled in an ice bath, followed by the addition of ether (300 mL) and dropwise addition of 5N sodium hydroxide solution until a large white precipitate was formed. The suspension was filtered, the filtrate was dried with anhydrous potassium carbonate, filtered again and concentrated by rotary evaporation to give tetrahydropyran-4-ethanol (17.7 g, 100% yield) as a colorless liquid.

References

[1] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9909 - 9911
[2] Patent: US2004/220214, 2004, A1
[3] Patent: WO2013/37960, 2013, A1. Location in patent: Page/Page column 76
[4] Patent: US9481674, 2016, B1. Location in patent: Page/Page column 31; 32
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 23, p. 6309 - 6323

2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL(4677-18-3)Related Product Information

• Tetrahydropyran-4-carbaldehyde
• 4-Amidinotetrahydro-2H-pyran hydrochloride
• Tetrahydropyran-4-boronic acid pinacol ester
• Tetrahydro-4-pyranol
• Tetrahydropyranyl-4-acetic acid
• Methyl tetrahydropyran-4-carboxylate
• Tetrahydro-4H-pyran-4-one
• Tetrahydro-2H-pyran-4-carboxylic acid
• TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE
• Tetrahydro-pyran-4-yl)-hydrazine
• TETRAHYDRO-PYRAN-3-CARBALDEHYDE
• Ethyl Tetrahydropyran-4-Carboxylate
• 4-(Dimethylamino)tetrahydro-2H-pyran
• TETRAHYDRO-2H-PYRAN-3-CARBOXYLIC ACID
• 4-Aminotetrahydro-2H-pyran acetate
• [(Tetrahydro-2H-pyran-4-yl)methyl]hydrazine dihydrochloride
• ETHYL TETRAHYDROPYRAN-4-YL-ACETATE
• TETRAHYDROFURAN-3-CARBOXALDEHYDE 98