Water → 1-Fluorenemethanol

HRID 1274218Notes

Reaction equation

HRID 1274218 reaction equation
[C:1]1([C:14](O)=[O:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80468Fluorene-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 523071-Fluorenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0°), stirred, solution of 1-fluorenecarboxylic acid (2.10 g, 10.0 mmol) in dry tetrahydrofuran (20 ml) under argon was added lithium aluminium hydride (0.19 g, 5 mmol) added in portions over 10 minutes. After a further 1 hour, water was added cautiously until effervescence ceased. The reaction mixture was partitioned between ethyl acetate and water and filtered. The organic layer was washed with saturated sodium hydrogen carbonate solution followed by water and dried over MgSO4. Evaporation of solvent gave crude product. δH (CDCl3 containing CD3OD) 3.87 (2H, s), 4.81 (2H, s), 7.2-7.75 (7H, m) ppm

Workup

  1. temperatureTo a cooled (0°)
  2. additionadded in portions over 10 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. filtrationfiltered
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate solution
  6. dry with materialdried over MgSO4
  7. customEvaporation of solvent
  8. customgave crude product

Sources & evidence

ORD record
ord-97ae396495fc460887d69f1040f01230
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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