Sodium Hydroxide → 9,9'-Spirobi[fluorene]-2,2'-dicarboxylic acid

HRID 2416291Notes

Reaction equation

HRID 2416291 reaction equation
BrBr.[C:3]([C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]3([C:30]4[CH:29]=[C:28]([C:31](=[O:33])C)[CH:27]=[CH:26][C:25]=4[C:24]4[C:19]3=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:8]=2[CH:7]=1)(=[O:5])C.[OH-:34].[Na+].S([O-])(O)=[O:37].[Na+]>O.O1CCOCC1>[CH:29]1[C:30]2[C:9]3([C:8]4[CH:7]=[C:6]([C:3]([OH:5])=[O:34])[CH:18]=[CH:17][C:16]=4[C:15]4[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]=2[CH:26]=[CH:27][C:28]=1[C:31]([OH:33])=[O:37]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 113615852,2'-diacetyl-9,9'-spirobifluoreneHCID 23665763Sodium Bisulfite

Product 1

HCID 52599819,9'-Spirobi[fluorene]-2,2'-dicarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

 While stirring. first 7.2 g of bromine and then a solution of 3.0 g of 2,2′-diacetyl-9,9′-spirobifluorene in a little dioxane were added dropwise at 0° C. to a solution of 6.0 g of sodium hydroxide in 30 ml of water. After stirring for a further hour at room temperature, the clear yellow solution was admixed with 1 g of sodium hydrogen sulfite dissolved in 20 ml of water. After acidification with concentrated HCl, the colorless product which precipitated was filtered off and washed with a little water. Recrystallization from ethanol gave 9,9′-spirobifluorene-2,2′-dicarboxylic acid as clear, colorless prisms (mp. 352° C.).

Workup

  1. stirringAfter stirring for a further hour at room temperature
  2. customAfter acidification with concentrated HCl, the colorless product which precipitated
  3. filtrationwas filtered off
  4. washwashed with a little water
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-ba72f387102e421d87079845d90b8dd8
Source dataset
uspto-grants-2004_11
Patent number
US06822094B2

Reaction notes

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