Hydrochloric Acid → 9-(hydroxymethyl)-9H-fluorene-2-carboxylic acid

HRID 1399378Notes

Reaction equation

HRID 1399378 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH:17]=[O:18])[C:6]=2[CH:5]=1)([OH:3])=[O:2].[BH4-].[Na+].Cl>O>[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH2:17][OH:18])[C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 592023689-formyl-9H-fluorene-2-carboxylic acid

Product 1

HCID 592023639-(hydroxymethyl)-9H-fluorene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Carboxy-9-formylfluorene (2.77 g, 0.012 mole) and distilled water (110 mL) were added to a round bottom flask. Sodium borohydride (8.65 g, 0.228 mole) was added slowly to the reaction solution. After approximately twenty minutes additional sodium borohydride (8.65 g, 0.228 mol) was added. After approximately 16 hours at room temperature, 1 M hydrochloric acid was added until the pH of the solution was approximately 2. The product was filtered and rinsed with distilled water. The 2-carboxy-9-hydroxymethylfluorene was dried under reduced pressure with either phosphorus pentoxide or drierite present. NMR confirmed the structure by the disappearance of the aldehyde proton and the appearance of a multiplet (three protons) centered at δ4.05 ppm, which is consistent with the proton at C-9 and the methylene of the hydroxymethyl group.

Workup

  1. additionwere added to a round bottom flask
  2. filtrationThe product was filtered
  3. washrinsed with distilled water
  4. dry with materialThe 2-carboxy-9-hydroxymethylfluorene was dried under reduced pressure with either phosphorus pentoxide or drierite present

Sources & evidence

ORD record
ord-d44c9c85f3c14e1189f91a7c53c132de
Source dataset
uspto-grants-2014_12
Patent number
US08905235B2

Reaction notes

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