Acetone → HCID 86583597, compound

HRID 277628Notes

Reaction equation

Cl[CH2:2][CH:3]1[CH2:5][O:4]1.C(=O)([O-])[O-:7].[K+].[K+].[CH2:12]([C:14](C)=[O:15])[CH3:13].C(#N)C.[CH3:20][C:21]([CH3:23])=[O:22]>>[O:4]1[C:5]2[C:3]1([CH2:20][CH:21]1[O:22][CH2:23]1)[CH:2]([CH:13]=[CH:12][C:14]=2[OH:15])[OH:7]

Participants

Reactant 5

HCID 180Acetone

HCID 6342Acetonitrile

HCID 6569Methyl Ethyl Ketone

HCID 7835Epichlorohydrin

HCID 11430Potassium Carbonate

Product 1

HCID 86583597HCID 86583597, compound

Procedure

Then, this is reacted with chloromethyloxirane in the presence of a deacidification agent, e.g. potassium carbonate, in acetone, methyl ethyl ketone or acetonitrile to form (2,3-epoxy)glycidylhydroquinone derivative (VIII). 1-(2,3,5-trimethyl-4-acetoxyphenoxy)-2,3-epoxypropane, in particular, can be synthesized by a method described in Czechoslovak Patent No.7704666. Then this is subjected to addition reaction with a phenylpiperazine derivative in heated alcohol or dioxane to form compound (XI), the protecting acyl or benzyl group of which then is cleaved with a base or by catalytic reduction to give the present compound, a hydroquinone derivative (II).

Sources & evidence

ORD record: ord-b57c567d94dc43ab8b93aa6d74ca37f1
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358515B2

Reaction notes

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