Sodium Hydroxide → 1-Methylfluorene

HRID 1918429Notes

Reaction equation

HRID 1918429 reaction equation
[CH3:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.I.[OH-].[Na+]>C(O)(=O)CC.O>[CH3:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 126958751-Methyl-9H-fluoren-9-one2×

Product 2

HCID 156041-MethylfluoreneYield 97%HCID 126958751-Methyl-9H-fluoren-9-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1032Propionic AcidSolvent

Procedure

1-Methylfluoren-9-one (46) was prepared according to Mortier et al. (D. Tilly, S. S. Samanta, A.-S. Castanet, A. De, J. Mortier, Eur. J. Org. Chem. 2005, 174). 1-Methylfluoren-9-one (46) was reduced according to the general procedure of Carruthers et al. (W. Carruthers, D. Whitmarsh, J. Chem. Soc. Perkin Trans, I 1973, 1511). 1-Methylfluoren-9-one (46) (6.8 g, 35 mmol) was dissolved in 450 ml propionic acid. Red phosphorus (7.4 g) and 100 ml concentrated HI were added and the reaction mixture was refluxed for 24 h. Quantitative conversion was shown by TLC. The reaction mixture was diluted with 500 ml water, neutralized with NaOH and extracted with Et2O (4×125 ml). The combined organic layers were washed with brine (2×125 ml), dried over MgSO4, filtered and the volatiles removed in vacuo to afford 6.1 g (97%) 47 as a white solid. The analytical data were consistent with the literature (G. L. Grunewald, A. E. Carter, D. J. Sall, J. A. Monn, J. Med. Chem. 1988, 31, 60 and M. J. Shapiro, J. Org. Chem. 1978, 43, 3769).

Workup

  1. temperaturethe reaction mixture was refluxed for 24 h
  2. extractionextracted with Et2O (4×125 ml)
  3. washThe combined organic layers were washed with brine (2×125 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-b7d3e818915d420e99e55a6822e2cdfd
Source dataset
uspto-grants-2013_12
Patent number
US08618328B2

Reaction notes

Loading…