1-Butanol → HCID 240120, compound

HRID 482140Notes

Reaction equation

[C:1]1([CH2:7][CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([OH:14])[CH2:11][CH2:12][CH3:13].S([O-])([O-])(=O)=O.[Mg+2]>>[CH2:6]([O:9][CH:8]([O:14][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:1][CH2:2][CH3:3]

Participants

Reactant 3

HCID 2631-Butanol

HCID 998Phenylacetaldehyde

HCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 240120HCID 240120, compoundYield 172.1%

Conditions

Temperature: 100 °C

Procedure

In a 100-ml three-necked flask, 24 g (0.2 mole) of phenylacetaldehyde, 18 g (0.24 mole) of n-butanol, 10 g of anhydrous magnesium sulfate and 0.1 mg of stannous chloride dihydrate were charged. The resulting mixture was stirred at 100° C. under atmospheric pressure for 6 hours in a nitrogen atmosphere. After the removal of magnesium sulfate, the residue was purified by chromatography on a silica gel column to give 43.1 g of phenylacetaldehyde dibutyl acetal [R1 =a benzyl group, R2 =a hydrogen atom and R3 =an n-butyl group] (yield: 86.3%).

Workup

customAfter the removal of magnesium sulfate
customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-5bad6e3c18e44b40903a35a086ddbabc
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05792876

Reaction notes

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