Phenol → HCID 19959608, compound

HRID 275078Notes

Reaction equation

HRID 275078 reaction equation
[N+]([C:4]1[C:21]2[C:20](=[O:22])[C:19]3[C:10](=[CH:11][C:12]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:9](=[O:23])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].[C:30]1([OH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CS(C)=O>[O:36]([C:4]1[C:21]2[C:20](=[O:22])[C:19]3[C:10](=[CH:11][C:12]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:9](=[O:23])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 20089827HCID 20089827, compound

Product 1

HCID 19959608HCID 19959608, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3 g (9.9 mmol) of 1-nitronaphthacene-5,12-dione (Example 42), 2.73 g (19.8 mmol) of potassium carbonate, 1.39 g (14.8 mmol) of phenol and 30 ml of DMSO are stirred at a bath temperature of 100° C. for 6 hours. After cooling, the mixture is partitioned between methylene chloride/dilute hydrochloric acid. The organic phase is separated off, washed with water, dried over sodium sulfate and evaporated. The product is obtained in a pure form by chromatography on silica gel (mobile phase: methylene chloride); yield 2.52 g (73%); melting point 195°-200° C.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between methylene chloride/dilute hydrochloric acid
  3. customThe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe product is obtained in a pure form by chromatography on silica gel (mobile phase: methylene chloride)

Sources & evidence

ORD record
ord-b59ddf0603bc4c8695acfbd1f7b18b0c
Source dataset
uspto-grants-1995_02
Patent number
US05391749

Reaction notes

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