Formaldehyde → 1-Fluorenemethanol

HRID 1641987Notes

Reaction equation

HRID 1641987 reaction equation
[CH:1]1[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.C=O.O.[C:17](=O)(O)[O-:18].[Na+]>C1COCC1>[C:1]1([CH2:17][OH:18])[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 712FormaldehydeHCID 6853FluoreneHCID 86585896Sodium bicarbonate water

Product 1

HCID 523071-Fluorenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Fluorene 60 g (0.36 mol) was dissolved in dehydrated THF 1500 ml. Subsequently, butyl lithium-hexane solution 225 ml (1.6 M) was slowly dropped in at 0° C. under argon gas atmosphere. Next, paraformaldehyde 12 g was added and the mixture was agitated at a room temperature for 5 hours. After agitation, saturated sodium bicarbonate water 600 ml was added, and extracted with diethyl ether. An organic layer was washed twice with an aqueous saturated NaCl solution, and then the solvent was evaporated off after drying using anhydrous magnesium sulfate. The obtained pasty solid matter was refined by recrystallization with a mixed solvent of hexane and ethanol to obtain a white needle crystal 50 g of fluorenyl methanol. It was determined by measurement of 1H-NMR that the obtained compound had a structure illustrated in the above-described formula (6). The melting point and the measurement result of 1H-NMR will be shown in the following paragraph.

Workup

  1. additionSubsequently, butyl lithium-hexane solution 225 ml (1.6 M) was slowly dropped in at 0° C. under argon gas atmosphere
  2. extractionextracted with diethyl ether
  3. washAn organic layer was washed twice with an aqueous saturated NaCl solution
  4. customthe solvent was evaporated off
  5. customafter drying
  6. customThe obtained pasty solid matter was refined by recrystallization with a mixed solvent of hexane and ethanol

Sources & evidence

ORD record
ord-a0011fb1addc430abcfe230647641eb6
Source dataset
uspto-grants-2012_02
Patent number
US08119323B2

Reaction notes

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