1-Methyl-9-fluorenecarboxylic acid → 1-Methyl-9-fluorenemethanol

HRID 1089838Notes

Reaction equation

HRID 1089838 reaction equation
[CH3:1][C:2]1[C:14]2[CH:13]([C:15](O)=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH3:1][C:2]1[C:14]2[CH:13]([CH2:15][OH:16])[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

3

Reactant 1

HCID 199784101-Methyl-9-fluorenecarboxylic acid

Product 1

HCID 199784261-Methyl-9-fluorenemethanolYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-9-fluorenecarboxylic acid (4.0 g, 17.9 mmol) in 100 mL of THF was charged with IM THF solution of BH3 -THF complex (35 mL, 35 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched with water (20 mL). The organic layer was washed with 10% potassium carbonate solution, water, brine, dried and evaporated to afford 1-methyl-9-fluorenemethanol (3.2 g, 84.9%).

Workup

  1. customthen quenched with water (20 mL)
  2. washThe organic layer was washed with 10% potassium carbonate solution, water, brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-61ea44da7ab4481ea4bc3f76fed1bac5
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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