Acetone → HCID 23149285, compound

HRID 2375249Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH:20]=[CH2:21].[CH3:22][C:23]([CH3:25])=[O:24]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:18][CH2:19][CH:20]=[CH2:21])=[C:6]([CH:7]([OH:8])[CH2:22][C:23](=[O:24])[CH3:25])[CH:9]=1

Participants

Reactant 4

HCID 180Acetone

HCID 11430Potassium Carbonate

HCID 21241Homoallyl bromide

HCID 728635-Bromosalicylaldehyde

Product 1

HCID 23149285HCID 23149285, compound

Procedure

To 300 ml of acetone there are added 10 g of 5-bromo-2-hydroxybenzaldehyde (49.7 mmol), 13.7 g of potassium carbonate (99.5 mmol) and 10.1 ml of 4-bromobut-1-ene (99.5 mmol); the reaction mixture is then heated at reflux for 36 hours before being cooled, filtered and evaporated to dryness to yield 4-[5-bromo-2-(but-3-en-1-yloxy)phenyl]-4-hydroxybutan-2-one in the form of an oil.

Workup

temperaturethe reaction mixture is then heated
temperatureat reflux for 36 hours
temperaturebefore being cooled
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-4645f6df99704555ab622c2cd91148d7
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465733B2

Reaction notes

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