Tetrahydropyranyl-4-acetic acid Chemical Properties

Melting point:

48-50°C

Boiling point:

285.1±13.0 °C(Predicted)

Density 

1.111±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

4.60±0.10(Predicted)

color 

White

CAS DataBase Reference

85064-61-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-36/37/39-22-39

RIDADR 

1759

Hazard Note 

Irritant/Keep Cold

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29329990

Tetrahydropyranyl-4-acetic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Tetrahydropyranyl-4-acetic acid is mainly used as a protecting agent in organic synthesis, especially in the multi-step complex synthesis of organic molecules to protect functional groups such as hydroxyl or amino groups.

Synthesis

General procedure for the synthesis of tetrahydropyran-4-acetic acid from ethyl tetrahydropyran-4-yl-acetate: 1. a solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a methanolic solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) at 0 °C or lower. 2. The mixture was stirred at room temperature for 15 hours. 3. The solvent was removed from the reaction mixture by depressurized distillation. 4. The aqueous layer was adjusted to pH 3 by adding 1 M hydrochloric acid and extracted with ethyl acetate. 5. Wash the organic layer with saturated brine and dry with anhydrous sodium sulfate. 6. The filtrate was concentrated under pressure to give tetrahydropyran-4-acetic acid as a colorless solid (12.0 g, 94%). This compound can be used in the next step without further purification. 7. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of tetrahydropyran-4-acetic acid (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature. 8. The mixture was refluxed for 48 hours. 9. The solvent was removed from the mixture by decompression distillation and the residue was diluted with water and extracted with dichloromethane. 10. The organic layer was dried over anhydrous sodium sulfate. 11. The filtrate was concentrated under pressure and the residue was chromatographed on a silica gel column (hexane: ethyl acetate = 9:1) to afford benzyl tetrahydropyran-4-acetate as an oil (12.0 g, 75% yield). 12. 12. Product characterization data: 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+).

References

[1] Patent: EP2737900, 2014, A1. Location in patent: Paragraph 0114; 0117-0118
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 16, p. 2300 - 2310
[3] Patent: US5221671, 1993, A
[4] Patent: EP1019398, 2004, B1. Location in patent: Page 51

Tetrahydropyranyl-4-acetic acid(85064-61-5)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Aminotetrahydropyran
• Tetrahydropyran
• Tetrahydro-4H-pyran-4-one
• Ethyl acetate
• Tetrahydro-2H-pyran-4-carboxylic acid
• ETHYL TETRAHYDROPYRAN-4-YL-ACETATE
• (TETRAHYDRO-FURAN-3-YL)-ACETIC ACID
• (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL
• Tetrahydropyran-4-carbaldehyde
• 2-(TETRAHYDRO-2H-PYRAN-4-YL)ACETAMIDE
• (TETRAHYDRO-PYRAN-4-YL)-ACETALDEHYDE
• 1,1-Dioxo-tetrahydro-thiopyran-4-one
• Tetrahydrothiopyran-4-one
• Tetrahydro-4-pyranol
• TETRAHYDRO-2H-PYRAN-4-YLACETYL CHLORIDE
• Tetrahydro-4H-Pyran-4-one
• TETRAHYDROPYRAN-2-METHANOL