Hydrochloric Acid → 9,9'-Spirobi[fluorene]-2,2'-dicarboxylic acid

HRID 635123Notes

Reaction equation

HRID 635123 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+].Cl>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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 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

At 0° C., first 7.2 g of bromine and then a solution of 3.0 g of 2,2′-diacetyl-9,9′-spirobifluorene in a small amount of dioxane were added dropwise with stirring to a solution of 6.0 g of sodium hydroxide in 30 ml of water. After the mixture had been stirred for a further 1 hour at room temperature, 1 g of sodium hydrogensulfite, dissolved in 20 ml of water, was added to the clear yellow solution. Following acidification with conc. hydrochloric acid, the colorless product which had precipitated out was filtered off and washed with a small amount of water. Recrystallization from ethanol produced 9,9′-spirobifluorene-2,2′-dicarboxylic acid as water-clear prisms (m.p. 352° C.).

Workup

  1. additionwas added to the clear yellow solution
  2. customthe colorless product which had precipitated out
  3. filtrationwas filtered off
  4. washwashed with a small amount of water
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-6152192a9cad482992452e70094e2ffc
Source dataset
uspto-grants-2001_02
Patent number
US06187224B1

Reaction notes

Loading…