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ChemicalBook CAS DataBase List 6-HYDROXYHEXANOIC ACID METHYL ESTER
4547-43-7

6-HYDROXYHEXANOIC ACID METHYL ESTER synthesis

14synthesis methods
-

Yield:4547-43-7 100%

Reaction Conditions:

Stage #1: hexahydro-2H-oxepin-2-onewith sulfuric acid in methanol; for 0.5 h;Reflux;
Stage #2: with water;sodium hydroxide in methanol;

Steps:

1

A solution of ε-caprolactone (25 g, 220 mmoles) in MeOH (25 ml) was added to a solution of 97% H2SO4 (2.5 ml) in MeOH (25 ml). The mixture was heated under reflux for 30 minutes. After that time, the mixture was neutralized with an aqueous solution of 10% NaOH (17.5 ml) and extracted with AcOEt (3 * 25 ml). The organic phase was dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure, obtaining (32 g, quantitative yield) methyl 6-hydroxyhexanoate (4), which was used in the following step without purifying. 1H-NMR (200 MHz, CDCl3). δ 3.55 (3H, s, -OCH3), 3.53 (2H, t, J = 6.2 Hz, H-6), 2.22 (2H, t, J= 7.2 Hz, H-2),1.62-1.23 (6H, m, -CH2-).

References:

EP2287146,2011,A1 Location in patent:Page/Page column 16

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