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ChemicalBook CAS DataBase List 2-Methyl-tetrahydro-pyran-4-ol
89791-47-9

2-Methyl-tetrahydro-pyran-4-ol synthesis

4synthesis methods
By the procedure of Ernst Hanschke (Chem. Ber., 1955, 88, 1053-1059), the acetaldehyde (1 equiv) and 3-buten-l-ol (1 equiv) are combined with 20% H2SO4 (10 vol) in a pressure tube. The tube was sealed and the reaction mixture was heated to 80 °C for 3 h. Reaction progress is monitored by TLC. After that, the reaction mixture is allowed to cool to rt, carefully neutralized (pH 8-9) by the coned ammonia, and extracted with EtOAc (3 x 5 vol). The combined organic phases are dried (Na2SO4), filtered, and the filtrate coned in vacuo providing the desired product 2-Methyl-tetrahydro-pyran-4-ol.
2-Methyl-tetrahydro-pyran-4-ol
-

Yield: 7.5 g

Reaction Conditions:

with sulfuric acid at 85; for 48 h;

Steps:

17 Description 172-Methyltetrahydro-2H-pyran-4-ol (D17)
Description 172-Methyltetrahydro-2H-pyran-4-ol (D17)A mixture of but-3-en-1-ol (7.21 g), 2,4,6-trimethyl-1,3,5-trioxane (4.40 g) and 20% H2S04 (12 g)was heated to 85°C for 2 days. The mixture was cooled to RT and extracted with ether (4x50 mL).Combined organic layer was dried and evaporated to afford the title compound (7.5 g). MS (El):C6H,202 requires 116; found 116 [Mj.

References:

GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED;GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED;DENG, Jing;LEI, Hui;MA, Xin;LIN, Xichen WO2015/180612, 2015, A1 Location in patent:Page/Page column 47