HCID 68815665, compound → HCID 57913420, compound

HRID 1261741Notes

Reaction equation

HRID 1261741 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH3:50])=[CH:44][CH:43]=2)(OC)[C:11]2[CH:16]=[C:15]([OH:17])[C:14]([C:18]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[CH:32][CH:31]=3)([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=3)OC)=[CH:13][C:12]=2[OH:39])=[CH:6][CH:5]=1)[CH3:2]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:37]([O:36][C:33]1[CH:34]=[CH:35][C:30]2[C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=3)=[C:14]3[C:15](=[CH:16][C:11]4[C:12]([O:39][C:43]5[C:42]([C:10]=4[C:7]4[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=4)=[CH:47][CH:46]=[C:45]([O:48][CH2:49][CH3:50])[CH:44]=5)=[CH:13]3)[O:17][C:31]=2[CH:32]=1)[CH3:38]

Participants

3

Reactant 1

HCID 68815665HCID 68815665, compound

Product 1

HCID 57913420HCID 57913420, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
195 °C

Procedure

Synthesis of the precursor 2,5-Bis-[bis-(4-ethoxy-phenyl)-methoxy-methyl]-benzene-1,4-diol: This compound is prepared in an analogous manner as described in example 9. From 10.16 g of 1,4-bis-(1-ethoxy-ethoxy)-benzene (40 mmol) and bis-(4-ethoxy-phenyl)-methanone (21.6 g, 80 mmol) 17.95 g (66%) of the product is obtained. b) A flask is charged with 2,5-Bis-[bis-(4-ethoxy-phenyl)-methoxy-methyl]-benzene-1,4-diol (16.97 g, 25 mmol) and nitrobenzene (30 ml) and heated at 195° C. (bath temperature) for two hours. The dark violet coloured mixture is then allowed to cool to ambient temperature. The product is then filtered off, and washed for three times with nitrobenzene (ca. 7 ml each time) and three times with toluene (ca. 8 ml each time) and finally dried in vacuum to give the product as deep violet crystals, 6.03 g (39%). The DSC of this material shows a mp. of 302° C. The structure of the material was confirmed by X-ray crystallography; space group: P-1; a=7.483(6); b=8.710(7); c=12.618(7); α=91.22(5) β=92.43(5) γ=110.35(5).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe product is then filtered off
  3. washwashed for three times with nitrobenzene (ca. 7 ml each time) and three times with toluene (ca. 8 ml each time)
  4. customfinally dried in vacuum

Sources & evidence

ORD record
ord-5c3d2680a04247dd8fdf5e36c0f996d9
Source dataset
uspto-grants-2013_06
Patent number
US08471019B2

Reaction notes

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