Sodium Hydroxide → 6-Chloroflavanone

HRID 1462951Notes

Reaction equation

HRID 1462951 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH:17]=1)[C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:17]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:18][CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:8][C:7]2=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1210655′-Chloro-2′-hydroxychalcone

Product 1

HCID 2366186-Chloroflavanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5'-Chloro-2'-hydroxychalcone (25.0 g) was dissolved in ethanol (125 ml.) and and aqueous solution of 1.5% sodium hydroxide (375 ml.) was added. The mixture was stirred at room temperature for 4 hrs. and the solid filtered off, washed with water and dried to give 6-chloroflavanone (16.65. g), mp. 90°-93° C. A sample recrystallised from 60°-80° C. petroleum ether had m.pt 95°-96° C. The flavanone (4.0 g) was dissolved in acetic acid (160 ml.) and concentrated hydrochloric acid (20 ml.) and added to amalgamated zinc (from zinc dust (40 g.) and mercuric chloride (0.5 g). The mixture was stirred for 1 hr., and allowed to stand overnight. The residual zinc was filtered off, and the filtrate diluted with water. The oily precipitate was extracted into either and the extract washed with water and saturated sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on alkaline alumina, eluting with 60°-80° C. petroleum either, to give 6-chloroflavan (0.52 g.), m.p. 71°-72° C.

Workup

  1. filtrationand the solid filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-36062ff791994980bc05d27649fb783f
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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