HCID 22451518, compound → HCID 15390710, compound

HRID 2185634Notes

Reaction equation

HRID 2185634 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH:6]=[CH:7][C:8]2=O)=[CH:4][CH:3]=1>O.Cl.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[OH:11]

Participants

5

Reactant 1

HCID 22451518HCID 22451518, compound

Product 1

HCID 15390710HCID 15390710, compoundYield 69.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

3.2 g of 6-chloro-7-hydroxy-1H-inden-1-one in 16.8 ml of water and 67.2 ml of concentrated aqueous hydrochloric acid were stirred and heated with freshly prepared zinc amalgame (from 26.88 g of zinc wool) in an oil bath at 120° C. for 16 hours. The reaction mixture was cooled, decanted and treated with ethylacetate and dichloromethane. The organic layer was evaporated in vacuo. The residue was purified by an acid/base separation yielding 2.08 g of 5-chloro-2,3-dihydro-1H-inden-4-ol, M.S. (C.I.) (M/Z): 169 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customdecanted
  3. additiontreated with ethylacetate and dichloromethane
  4. customThe organic layer was evaporated in vacuo
  5. customThe residue was purified by an acid/base separation

Sources & evidence

ORD record
ord-ba444bc170e64934bed0f66ce237649b
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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