Bis(4-hydroxyphenyl)methane → 1,1'-(Methylenedi-p-phenylene)bismaleimide

HRID 1893067

Reaction equation

HRID 1893067 reaction equation
[CH:1]1[C:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11](O)=[CH:12][CH:13]=2)=[CH:5][CH:4]=[C:3](O)[CH:2]=1.CC1C([N:26]2[C:30](=[O:31])[CH:29]=[CH:28][C:27]2=[O:32])=C(C=CC=1)C(Cl)=O>C(N(CC)CC)C.ClCCCl>[CH:1]1[C:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([N:26]3[C:30](=[O:31])[CH:29]=[CH:28][C:27]3=[O:32])=[CH:12][CH:13]=2)=[CH:5][CH:4]=[C:3]([N:26]2[C:27](=[O:32])[CH:28]=[CH:29][C:30]2=[O:31])[CH:2]=1

Participants

5

Reactant 2

HCID 12111Bis(4-hydroxyphenyl)methaneHCID 87470001Methyl maleimidobenzoyl chloride

Product 1

HCID 836481,1'-(Methylenedi-p-phenylene)bismaleimide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A 6.0 g quantity of 4,4′-dihydroxydiphenylmethane is dissolved in a solution of 12.6 ml of triethylamine in 50 ml of 1,2-dichloroethane in a 250 ml flask. To the solution is slowly added a solution of 15.5 g of methyl maleimidobenzoyl chloride in 50 ml of 1,2-dichloroethane. The mixture is allowed to react at room temperature for 16 hr. The reaction mixture is precipitated in water, filtered under reduced pressure, washed sequentially with water and ethanol, and dried at 60° C. under vacuum for 48 hr, yielding the bismaleimide compound of Formula 20m.

Workup

  1. customto react at room temperature for 16 hr
  2. customThe reaction mixture is precipitated in water
  3. filtrationfiltered under reduced pressure
  4. washwashed sequentially with water and ethanol
  5. customdried at 60° C. under vacuum for 48 hr

Sources & evidence

ORD record
ord-0b52e23c04354260b8fc09e02c6e2208
Source dataset
uspto-grants-2013_08
Patent number
US08512596B2

Linked notes

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