Methyl iodide → 9-(Methoxymethyl)-9H-fluorene-9-methanol

HRID 2416159

Reaction equation

HRID 2416159 reaction equation
[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.I[CH3:19].[H-].[Na+]>O1CCCC1>[CH3:19][O:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3450229H-Fluorene-9,9-dimethanol

Product 1

HCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere and anhydrous condition, to a reactor were added in succession 80 ml of tetrahydrofuran, 22.6 g (0.1 mol) of 9,9-bis(hydroxymethyl)fluorene and 57 g (0.4 mol) of iodomethane. After the reaction mixture was admixed homogeneously by stirring, 4.6 g of 52% NaH in mineral oil (0.1 mol) was added batch-wise over 2 hours at room temperature, Upon completing the addition, the reaction mixture was stirred for further 2 hours. The unreacted iodomethane was recovered by distillation. The remainder was diluted with 100 ml of water, and extracted twice using 100 ml of diethyl ether for each time. The combined diethyl ether extract was dried over anhydrous sodium sulfate. After drying, thee ether solution was evaporated to dry to give 22.8 g of crude. The crude was purified through column chromatography to give 14.9 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (yield 62%).

Workup

  1. additionthe addition
  2. stirringthe reaction mixture was stirred for further 2 hours
  3. distillationThe unreacted iodomethane was recovered by distillation
  4. additionThe remainder was diluted with 100 ml of water
  5. extractionextracted twice
  6. extractionThe combined diethyl ether extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customAfter drying
  9. customthee ether solution was evaporated
  10. customto dry
  11. customto give 22.8 g of crude
  12. customThe crude was purified through column chromatography

Sources & evidence

ORD record
ord-d62ed08e665f431d83347205370dea20
Source dataset
uspto-grants-2004_11
Patent number
US06822109B2

Linked notes

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