1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Quinacridone

HRID 845559

Reaction equation

HRID 845559 reaction equation
[NH:1]([C:8]1[CH2:17][C:16]([C:18]([O:20]C)=O)=[C:15]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:14][C:9]=1[C:10]([O:12]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[CH:26]1[CH:27]=[C:28]2[C:18]([C:16]3[C:15]([NH:22][C:23]2=[CH:24][CH:25]=1)=[CH:14][C:9]1[C:10]([C:7]2[C:2]([NH:1][C:8]=1[CH:17]=3)=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:12])=[O:20]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)2×HCID 786101,4-Cyclohexadiene-1,4-dicarboxylic acid, 2,5-bis(phenylamino)-, 1,4-dimethyl ester

Product 1

HCID 13976QuinacridoneYield 89%

Conditions

Temperature
140 °C

Procedure

(b.1) A suspension of 37.8 parts of dimethyl 3,6-dihydro-2,5-dianilinoterephthalate in 200 parts of ®Dowtherm A is added dropwise to 150 parts of boiling ®Dowtherm A. The mixture is then kept at the boil for a further 90 minutes. After approx. 100 parts of the solvent have been distilled off, the mixture is cooled to approx. 140° C., after which 25.4 parts of iodine are added and the mixture is kept at the boil for a further 4 hours. Working up is effected as described earlier in the text under "Method A". 27.8 parts of quinacridone in the β-crystal phase are obtained, which corresponds to a yield of 89% of theory (relative to dimethyl 3,6-dihydro-2,5-dianilinoterephthalate.

Workup

  1. additionis added dropwise to 150 parts
  2. distillationhave been distilled off
  3. additionafter which 25.4 parts of iodine are added
  4. waitthe mixture is kept at the boil for a further 4 hours

Sources & evidence

ORD record
ord-3d8f5738a72c47d997233d9b488f6ece
Source dataset
uspto-grants-1988_07
Patent number
US04758664

Linked notes

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