ChemicalBook CAS DataBase List 4-FORMYL-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER

4-FORMYL-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER synthesis

6synthesis methods

Product Name:4-FORMYL-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER
CAS Number:37942-76-0
Molecular formula:C9H14O3
Molecular Weight:170.21

METHYL TRANS-4-HYDROXYMETHYLCYCLOHEXANECARBOXYLATE

13380-85-3
57 suppliers
$42.00/250mg

4-FORMYL-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER

37942-76-0
49 suppliers
inquiry

Yield: 99%

Reaction Conditions:

with sodium hydrogencarbonate;Dess-Martin periodane in dichloromethane at 20; for 2.5 h;

Steps:

88
Intermediate 88Methyl 4-formylcyclohexanecarboxylate; To a solution of methyl 4-(hydroxymethyl)cyclohexanecarboxylate (Intermediate 87, 4.08 g, 23.7 mmol) in DCM was added NaHCO₃(9.95 g, 118 mmol), followed by Dess-Martin Periodinane (12.1 g, 28.4 mmol). The mixture was stirred at r.t. for 2.5 h. Et₂O (60 mL) was added followed by an aq. solution of NaHCO₃(1 M, 60 mL) and a 20% aq. solution of sodium thiosulfate (40 mL). The resulting mixture was stirred overnight. The phases were separated and the aqueous phase was extracted with Et₂O. The organic phase was washed with brine and dried over MgSO₄, filtered and concentrated in vacuo to yield the title compound (4.0 g, 99% yield): MS (EI) m/z 170 M⁺.

References:

ASTRAZENECA AB US2012/165347, 2012, A1 Location in patent:Page/Page column 44