Water → HCID 12531832, compound

HRID 1863295Notes

Reaction equation

HRID 1863295 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:19]2[CH:20]=[CH:21][C:16]([C:14](=[O:15])[CH3:13])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 117874-Chloro-1-naphthol

Product 1

HCID 12531832HCID 12531832, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 35.6 g of 4-chloro-1-naphthol, 27.62 g of 4-fluoroacetophenone, and 55.2 g of potassium carbonate in 250 ml of N,N-dimethylacetamide are heated under Argon with vigorous stirring at 150°-155° C. overnight. After cooling to room temperature, 500 ml of water is added and the mixture is extracted with three 150 ml portions of benzene. The combined extracts are washed with two 150 ml portions of 5% NaOH, three 150 ml portions of 10% HCl, two 150 ml portions of water, 150 ml of saturated NaHCO3, 150 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent at reduced pressure affords a light brown solid, which is extracted with 800 ml of hot hexane to give the product as a tan solid, mp 98°-105° C. Recrystallization from 15:1 hexane-chloroform gives cream colored plates, mp 100°-104.5° C.

Workup

  1. temperatureare heated under Argon
  2. extractionthe mixture is extracted with three 150 ml portions of benzene
  3. washThe combined extracts are washed with two 150 ml portions of 5% NaOH, three 150 ml portions of 10% HCl, two 150 ml portions of water, 150 ml of saturated NaHCO3, 150 ml of saturated brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent at reduced pressure
  6. customaffords a light brown solid, which
  7. extractionis extracted with 800 ml of hot hexane

Sources & evidence

ORD record
ord-66a91d6580864a7b8b44a922287a5740
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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