2-Methoxyethanol → HCID 14350667, compound

HRID 2291536Notes

Reaction equation

HRID 2291536 reaction equation
Br[CH:2]1[C:14]2([CH2:15][CH2:16][CH3:17])[C:9](=[CH:10][C:11](=[O:18])[CH2:12][CH2:13]2)[C:8]2[C:3]1=[CH:4][C:5]([O:21][CH3:22])=[C:6]([Cl:20])[C:7]=2[Cl:19].C[O:24]CCO>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:19][C:7]1[C:6]([Cl:20])=[C:5]([O:21][CH3:22])[CH:4]=[C:3]2[C:8]=1[C:9]1[C:14]([CH2:15][CH2:16][CH3:17])([CH:2]2[OH:24])[CH2:13][CH2:12][C:11](=[O:18])[CH:10]=1

Participants

5

Reactant 2

HCID 80192-MethoxyethanolHCID 14350666HCID 14350666, compound

Product 1

HCID 14350667HCID 14350667, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A mixture of 9-bromo-5,6-dichloro-7-methoxy-9a-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (6.29 g, 0.0157 mole) and silver nitrate (7.89 g, 0.047 mol) in 2-methoxyethanol (200 ml) and H2O (100 ml) was heated at reflux for 2 hours, filtered and evaporated to dryness. Chromatography of the residue on silica gel eluted with ethyl acetate-hexane (1:1) gave 1.2 g of 5,6-dichloro-9-hydroxy-7-methoxy-9a-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one which melted at 173°-5° C. and was used in Step C without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered
  4. customevaporated to dryness
  5. washChromatography of the residue on silica gel eluted with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-2cc1674d035f41db96db4b8e3dee82ce
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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