Sodium Hydroxide → HCID 59561114, compound

HRID 1918435Notes

Reaction equation

HRID 1918435 reaction equation
[CH3:1][C:2]1[C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[CH3:16])[C:6]=2[CH:5]=[C:4]([CH3:17])[CH:3]=1.I.[OH-].[Na+]>C(O)(=O)CC.O>[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[CH3:16])[C:6]=2[CH:5]=[C:4]([CH3:17])[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 57909153HCID 57909153, compound2×

Product 1

HCID 59561114HCID 59561114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1032Propionic AcidSolvent

Procedure

1,3,8-Trimethylfluoren-9-one (53) was reduced according to the general procedure of Carruthers et al. (W. Carruthers, D. Whitmarsh, J. Chem. Soc. Perkin Trans, I 1973, 1511). 1,3,8-Trimethylfluoren-9-one (53) (2.74 g, 12.3 mmol) was dissolved in propionic acid (235 ml). Red phosphorus (3.0 g) and concentrated HI (40 ml) were added and the reaction mixture was refluxed for 24 h. Quantitative conversion was shown by TLC. The reaction mixture was diluted with water (250 ml), 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 2.56 g (quant.) 54 as a white solid.

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-3df40ec1fed24af089656ebffef515d4
Source dataset
uspto-grants-2013_12
Patent number
US08618328B2

Reaction notes

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