Hydrochloric Acid → HCID 12831967, compound

HRID 1903581Notes

Reaction equation

HRID 1903581 reaction equation
Cl.O.[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([Cl:14])[CH:13]=1)[O:10][CH2:9][CH2:8][C:7]2=O>[Zn].C1(C)C=CC=CC=1>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([Cl:14])[CH:13]=1)[O:10][CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 128319666-Bromo-8-chloro-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 12831967HCID 12831967, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 1140TolueneSolvent

Procedure

To the amalgam of zinc--prepared from 1280 g (19.7 gram-atoms) of zinc, 128 g (5.4×10-1M) of mercurous chloride, 64 cm3 of concentrated hydrochloric acid and 1900 cm3 of water--are added, in order, 1000 cm3 water, 1500 cm3 of concentrated hydrochloric acid, 3500 cm3 of toluene and 640 g (2.45 M) of 6-bromo-8-chloro-4-chromanone (III2). The mixture is refluxed for 1 hour and, after cooling and decantation, it is extracted with ether and washed in water up to neutrality. 305 g (yield=50%) of expected product are thus isolated. B.p.0.01 =128° C.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperatureafter cooling
  3. extractiondecantation, it is extracted with ether
  4. washwashed in water up to neutrality

Sources & evidence

ORD record
ord-0fe9e13c451e44e1a2d70070aa1b89c3
Source dataset
uspto-grants-1984_03
Patent number
US04436915

Reaction notes

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