ChemicalBook CAS DataBase List (1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate

(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate synthesis

4synthesis methods

Product Name:(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate
CAS Number:110928-44-4
Molecular formula:C9H16O3
Molecular Weight:172.22

15177-67-0 Synthesis

TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID MONOMETHYL ESTER

15177-67-0
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$6.00/1g

(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate

110928-44-4
102 suppliers
$19.00/100mg

Yield: 100%

Reaction Conditions:

Stage #1:trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid with borane-THF in tetrahydrofuran at -50 - -10; for 2 h;
Stage #2: with water;sodium hydrogencarbonate in tetrahydrofuran at 0;

Steps:

A.1.3 Reference Example A1
(3) Under argon gas atmosphere to a solution of momomethyl trans-cyclohexane-1,4-dicarboxylate (14.3 g) in tetrahydrofuran (78 mL) was added dropwise 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (100 mL) at -50 °C over a period of 1 hour and the mixture was stirred at -10 °C for 1 hour. To the reaction mixture was added water (160 mL) and an aqueous saturated sodium hydrogencarbonate solution (160 mL) under ice-cooling and the mixture was extracted with ethyl acetate (160 mL x 4). The extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by a flash column chromatography on silica gel (Solvent; chloroform/methanol = 20: 1) to give methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (13.25 g, yield: 100 %) as an oil. MS(APCI)m/z; 173 [M+H]⁺

References:

Location in patent:Page/Page column 55