2-Methoxy-9-fluorenecarboxylic acid → 2-Methoxy-9-fluorenemethanol

HRID 1089832Notes

Reaction equation

HRID 1089832 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]([C:16](O)=[O:17])[C:5]=2[CH:4]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]([CH2:16][OH:17])[C:5]=2[CH:4]=1

Participants

3

Reactant 1

HCID 199784192-Methoxy-9-fluorenecarboxylic acid

Product 1

HCID 199784172-Methoxy-9-fluorenemethanolYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-methoxy-9-fluorenecarboxylic acid (2.2 g, 9.2 mmol) in 100 mL of THF at 0° C. was charged with 1M THF solution of BH3 -THF complex (20 mL, 20 mmol). The reaction mixture was stirred overnight then quenched with 10 mL of 10% acetic acid in methanol an diluted with 100 mL of water. The layers were separated, the aqueous phase was extracted with ethyl acetate (3×25 mL). The combined extracts were dried over magnesium sulfate and evaporated. The residue was crystallized from methanol-water to afford 1.87 g (87.0%) of product.

Workup

  1. customthen quenched with 10 mL of 10% acetic acid in methanol
  2. additionan diluted with 100 mL of water
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was crystallized from methanol-water

Sources & evidence

ORD record
ord-6207452ddca04023a077b2f7db297134
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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