Benzoic Acid → HCID 67506256, compound

HRID 251716Notes

Reaction equation

HRID 251716 reaction equation
[C:1]12([C:11]3[C:12](=O)[C:13]4[C:21](=[CH:22][CH:23]=3)[C:20]3[C:15](=[CH:16][C:17]([C:24]56[CH2:33][CH:28]7[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]7)[CH2:25]5)[CH2:31]6)=[CH:18][CH:19]=3)[CH:14]=4)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:35]([OH:43])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[C:24]12([C:17]3[CH:18]=[CH:19][C:20]4[C:21]5[C:13](=[CH:12][C:11]([C:1]67[CH2:10][CH:5]8[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]8)[CH2:2]6)[CH2:8]7)=[CH:23][CH:22]=5)[C:14]([C:37]5[C:36]([C:35]([OH:43])=[O:42])=[CH:41][CH:40]=[CH:39][CH:38]=5)([C:41]5[C:36]([C:35]([OH:43])=[O:42])=[CH:37][CH:38]=[CH:39][CH:40]=5)[C:15]=4[CH:16]=3)[CH2:31][CH:30]3[CH2:32][CH:26]([CH2:27][CH:28]([CH2:29]3)[CH2:33]1)[CH2:25]2

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 67506337HCID 67506337, compoundHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 67506256HCID 67506256, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

In a 500 mL recovery flask, 44.9 g of 2,7-di(1-adamantyl)-fluorenone obtained in the same manner as in Synthesis example 7 (100 mmol), 36.6 g of benzoic acid (300 mmol), 203 mL of Eaton's reagent (7.7 wt % methanesulfonic acid solution of diphosphorus pentoxide) and a stirrer were charged and agitated at 150° C. for 12 hours under a nitrogen atmosphere. After reaction solution reached room temperature, mL of ion-exchange water was added slowly. An aqueous layer was separated and removed therefrom. Then, solvent was removed from the reaction solution under reduced pressure. Solid thus obtained was purified by column chromatography, thus obtaining 54.7 g of 2,7-di(1-adamantyl)-fluorene-9,9-bisbenzoic acid (81 mmol; yield: 81%).

Workup

  1. additionwere charged
  2. customAfter reaction solution
  3. customreached room temperature
  4. customAn aqueous layer was separated
  5. customremoved
  6. customThen, solvent was removed from the reaction solution under reduced pressure
  7. customSolid thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-aa19830375ae498f861f99381caea4dc
Source dataset
uspto-grants-2011_01
Patent number
US07863347B2

Reaction notes

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