Hydroxycaprylic Acid → Methyl 2-hydroxyoctanoate

HRID 278462Notes

Reaction equation

[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].[CH3:12]O.Cl>>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH3:12])=[O:4]

Participants

Reactant 2

HCID 94180Hydroxycaprylic Acid

HCID 21893726Hydrochloride methanol

Product 1

HCID 10487462Methyl 2-hydroxyoctanoate

Procedure

2-Hydroxyoctanoic acid (1.0 g) was stirred in 10% hydrogen chloride methanol solution (20 ml) at room temperature. After 1.5 hours, the reaction mixture was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with aqueous NaHCO3 solution and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gave methyl 2-hydroxyoctanoate (0.684 g) as a colorless oil.

Workup

customthe reaction mixture was evaporated under reduced pressure
customThe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with aqueous NaHCO3 solution
dry with materialdried over sodium sulfate
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-40c1c3396bad46d08b4711877faefc2a
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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