Hydrogen Bromide → 4-hydroxy-3-isopropylfuran-2(5H)-one

Reaction equation

BrC[C:3](=[O:13])[CH:4]([CH:10]([CH3:12])[CH3:11])[C:5]([O:7][CH2:8]C)=[O:6].Br>>[OH:13][C:3]1[CH2:8][O:7][C:5](=[O:6])[C:4]=1[CH:10]([CH3:11])[CH3:12]

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 86709464HCID 86709464, compound

Product 1

HCID 589802874-hydroxy-3-isopropylfuran-2(5H)-one

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 4-bromo-2-isopropyl-3-oxobutanoate (7.1 g, 28 mmol) and hydrogen bromide (48%, 0.032 mL, 0.28 mmol) was heated at 100° C. for 8 h. After cooling to rt, the solid was collected by filtration followed by diethyl ether washing to give 4-hydroxy-3-isopropylfuran-2(5H)-one. LC/MS: (M+1)+: 143.09.

Workup

temperatureAfter cooling to rt
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-8840b3c7e86745c68fdef7c57c601ecf
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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