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

HRID 356792Notes

Reaction equation

HRID 356792 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

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 are added dropwise at 0° C. while stirring 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 is admixed with 1 g of sodium hydrogen sulfite dissolved in 20 ml of water. After acidification with concentrated hydrochloric acid, the precipitated colorless product is filtered off and washed with a little water. Recrystallization with ethanol gives 9,9'-spirobifluorene-2,2'-dicarboxylic acid as clear prisms (m.p. 352° C.).

Workup

  1. filtrationAfter acidification with concentrated hydrochloric acid, the precipitated colorless product is filtered off
  2. washwashed with a little water
  3. customRecrystallization with ethanol

Sources & evidence

ORD record
ord-b12069a507aa4037876091f3f7b2f385
Source dataset
uspto-grants-1998_11
Patent number
US05840217

Reaction notes

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