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Tetrahydrophthalic anhydride → Vinyl isobutyl ether

HRID 34893
Notes
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Reaction equation

HRID 34893 reaction equation
[CH:1]12[C:10](=O)[O:9][C:7](=O)[CH:2]1CC=C[CH2:6]2.[Pd:12]([Cl:14])[Cl:13].[C:15](#[N:17])[CH3:16]>CN(C)C=O>[Pd:12]([Cl:14])[Cl:13].[CH2:10]([O:9][CH:7]=[CH2:2])[CH:1]([CH3:6])[CH3:15].[Pd:12]([Cl:14])[Cl:13].[C:15](#[N:17])[CH3:16].[CH:7]([O:9][CH2:10][CH:1]([CH3:6])[CH3:15])=[CH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6810Tetrahydrophthalic anhydrideHCID 11769946Acetonitrile palladium dichloride

Product 3

HCID 7992Vinyl isobutyl etherHCID 11769946Acetonitrile palladium dichlorideHCID 86739870Isobutylvinyl ether palladium dichloride

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

4-cyclohexene-1,2-dicarboxylic acid anhydride is dissolved in three times its quantity of dimethyl formamide. Its equimolar quantity of acetonitrile palladium dichloride is added at 40° C. in the course of 2 hours. Dimethyl formamide and acetonitrile are distilled off at 45° C./25 mbar. A brownish solid with a melting point of 53°-54° C. is obtained in a 90% yield. Isobutylvinyl ether palladium dichloride is obtained in analogous manner from acetonitrile palladium dichloride and isobutyl vinyl ether, melting point 57°-60° C.

Workup

  1. distillationDimethyl formamide and acetonitrile are distilled off at 45° C./25 mbar
  2. customA brownish solid with a melting point of 53°-54° C. is obtained in a 90% yield

Sources & evidence

ORD record
ord-64611501a50d4da39f62e11c152ff7cc
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764401

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes