Acetic Acid → HCID 59435076, compound

HRID 2195596Notes

Reaction equation

HRID 2195596 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][C:16]([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:15][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:16]3[CH:15]=[CH:14][C:13]([C:8]4[CH:9]=[C:10]5[C:5](=[CH:6][CH:7]=4)[C:4](=[O:34])[C:3]([OH:35])([OH:2])[C:11]5=[O:12])=[CH:18][CH:17]=3)[CH:20]=2)[C:24]1=[O:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 59435075HCID 59435075, compound

Product 1

HCID 59435076HCID 59435076, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,4-bis(2,2-dimethoxy-1,3-dioxoindan-5-yl)benzene (20) (209 mg, 0.429 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. The mixture was refluxed for 2 hours. It was then cooled to room temperature to deposit a solid, which was collected by filtration. The solid was washed with cold water and chloroform and vacuum dried to obtain 168 mg (91%) of 1,4-bis(2,2-dihydroxy-1,3-dioxoindan-5-yl)benzene (21) in the form of a light gray solid. The readings for this compound are as follows.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. filtrationwas collected by filtration
  3. washThe solid was washed with cold water and chloroform and vacuum
  4. customdried

Sources & evidence

ORD record
ord-76ea2e06bd35453484aeb6714d282ef0
Source dataset
uspto-grants-2012_12
Patent number
US08338028B2

Reaction notes

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