Acetic Acid → HCID 59435063, compound

HRID 2195599Notes

Reaction equation

HRID 2195599 reaction equation
C[O:2][C:3]1([O:35]C)[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:20]=[C:21]5[C:25](=[CH:26][CH:27]=4)[C:24](=[O:28])[C:23]([O:31]C)([O:29]C)[C:22]5=[O:33])[CH:14]=3)[CH:9]=2)[C:4]1=[O:34].C(O)(=O)C.Br>O>[OH:31][C:23]1([OH:29])[C:22](=[O:33])[C:21]2[C:25](=[CH:26][CH:27]=[C:19]([C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([C:8]4[CH:9]=[C:10]5[C:5](=[CH:6][CH:7]=4)[C:4](=[O:34])[C:3]([OH:2])([OH:35])[C:11]5=[O:12])[CH:14]=3)[CH:20]=2)[C:24]1=[O:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 59435064HCID 59435064, compound

Product 1

HCID 59435063HCID 59435063, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

1,3-bis(2,2-dimethoxy-1,3-dioxoindan-5-yl)benzene (33) (119 mg, 0.25 mmol) was suspended in a solvent mixture of 3 ml of acetic acid and 3 ml of water, and the suspension was mixed with 3 ml of 47% hydrobromic acid. This mixture was refluxed at 115° C. over night. After it was cooled to room temperature, the reaction solution was filtered to obtain a solid, which was then dried at a reduced pressure, to obtain 59 mg (56%) of 1,3-bis(2,2-dihydroxy-1,3-dioxoindan-5-yl)benzene (34) in the form of a beige solid. The readings for this compound are as follows.

Workup

  1. temperatureAfter it was cooled to room temperature
  2. filtrationthe reaction solution was filtered
  3. customto obtain a solid, which
  4. customwas then dried at a reduced pressure

Sources & evidence

ORD record
ord-a8a3f8edfb624abfae14cf60bfe5fd1f
Source dataset
uspto-grants-2012_12
Patent number
US08338028B2

Reaction notes

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