2,7-Dimethyl-9H-fluorene-9-carboxylic acid → (2,7-Dimethyl-9H-fluoren-9-yl)methanol

HRID 1089842Notes

Reaction equation

HRID 1089842 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([CH3:15])=[CH:9][CH:10]=3)[CH:5]([C:16](O)=[O:17])[C:4]=2[CH:3]=1>C1COCC1>[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([CH3:15])=[CH:9][CH:10]=3)[CH:5]([CH2:16][OH:17])[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 3483962,7-Dimethyl-9H-fluorene-9-carboxylic acid

Product 1

HCID 348427(2,7-Dimethyl-9H-fluoren-9-yl)methanolYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,7-dimethyl-9-fluorenecarboxylic acid (4.3 g, 18.0 mmol) in THF (100 mL) was charged with 1M THF solution of BH3 -THF complex (36.0 mL, 36.0 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched with water (100 mL) and HCl (3 mL). After addition of ethyl acetate (50 mL) the organic layer was separated and washed with 10% potassium carbonate solution, water, brine, dried over magnesium sulfate and evaporated to afford 2,7-dimethyl-9-fluorenemethanol (3.0 g, 74.4%).

Workup

  1. customthen quenched with water (100 mL) and HCl (3 mL)
  2. additionAfter addition of ethyl acetate (50 mL) the organic layer
  3. customwas separated
  4. washwashed with 10% potassium carbonate solution, water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-8a1659f12a6445a09c3581eb3121e6bc
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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