Iodine → 7-[(1-Naphthalenyl)methoxy]-2-heptanone

HRID 358918Notes

Reaction equation

HRID 358918 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[Mg].II.[C:22](OC(=O)C)(=[O:24])[CH3:23].[Cl-].[NH4+]>CCOCC>[C:9]1([CH2:8][O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:22](=[O:24])[CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 807IodineHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 191018421-[[(5-Bromopentyl)oxy]methyl]naphthalene

Product 1

HCID 191018287-[(1-Naphthalenyl)methoxy]-2-heptanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

1-[[(5-Bromopentyl)oxy]methyl]naphthalene (9.96 g) in dry ether (40 ml) was added to magnesium turnings (0.94 g) and iodine (one small crystal) under nitrogen with stirring at a rate which maintained a gentle reflux. The mixture was stirred at reflux for 30 min, cooled to ambient temperature and added over 2.5 h to acetic anhydride (7.67 ml) in ether (15 ml) at -78° under nitrogen with vigorous stirring. After 2 h at -78°, the mixture was allowed to warm to -10° and treated with aqueous saturated ammonium chloride (50 ml). Ether (50 ml) was added, the aqueous layer was separated and the ethereal layer was washed with 1M-aqueous sodium hydroxide (100 ml). The combined aqueous washings were extracted with ether (100 ml) and this extract was combined with the ethereal layer above. The dried ethereal solution was evaporated and the residual oil purified FCC. Elution with ether-cyclohexane (1:4) gave, after Kugelrohr distillation, the title compound as a colourless oil (3.39 g), b.p. 190°/0.3 Torr (Kugelrohr).

Workup

  1. temperaturemaintained a gentle reflux
  2. stirringThe mixture was stirred
  3. temperatureat reflux for 30 min
  4. temperatureto warm to -10°
  5. customthe aqueous layer was separated
  6. washthe ethereal layer was washed with 1M-aqueous sodium hydroxide (100 ml)
  7. extractionThe combined aqueous washings were extracted with ether (100 ml)
  8. customThe dried ethereal solution was evaporated
  9. customthe residual oil purified FCC
  10. washElution with ether-cyclohexane (1:4)
  11. customgave
  12. distillationafter Kugelrohr distillation

Sources & evidence

ORD record
ord-a2f0bfe9b7c74806bcdc9f94f68d9795
Source dataset
uspto-grants-1991_03
Patent number
US04997986

Reaction notes

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