Ethanol → HCID 15230859, compound

HRID 1464496Notes

Reaction equation

[C:1]1([CH:7]([C:13]2[C:14](=[O:23])[C:15]([CH3:22])=[C:16]([CH3:21])[C:17](=[O:20])[C:18]=2[CH3:19])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:28](O)[CH3:29]>>[C:1]1([CH:7]([C:13]2[C:14](=[O:23])[C:15]([CH3:22])=[C:16]([CH3:21])[C:17](=[O:20])[C:18]=2[CH3:19])[CH2:8][CH2:9][C:10]([O:12][CH2:28][CH3:29])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 14651334HCID 14651334, compound

Product 1

HCID 15230859HCID 15230859, compoundYield 84%

Procedure

4-Phenyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-butanoic acid (1.2 g) was dissolved in ethanol (50 ml), and thionyl chloride (0.4 ml) was added to the solution, followed by stirring at room temperature for 4 hours. After the reaction solution was concentrated under reduced pressure, the resulting residue was dissolved in isopropyl ether, and the organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a silica gel column, and the object compound was eluted with isopropyl ether to give ethyl 4-phenyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)butanoate (1.1 g, 84%). Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this example, the Compound No. 42 was prepared.

Workup

concentrationAfter the reaction solution was concentrated under reduced pressure
dissolutionthe resulting residue was dissolved in isopropyl ether
washthe organic layer was washed with water
customdried
concentrationconcentrated under reduced pressure
customThe residue was chromatographed on a silica gel column
washthe object compound was eluted with isopropyl ether

Sources & evidence

ORD record: ord-6096c53eba534ab9bfe7c64bbeb18f4a
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304658

Reaction notes

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