Acetic Acid → HCID 59435070, compound

HRID 2195598Notes

Reaction equation

HRID 2195598 reaction equation
C[O:2][C:3]1([O:50]C)[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[C:17]([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:16]=[C:15]([C:34]4[CH:35]=[C:36]5[C:40](=[CH:41][CH:42]=4)[C:39](=[O:43])[C:38]([O:46]C)([O:44]C)[C:37]5=[O:48])[CH:14]=3)[CH:9]=2)[C:4]1=[O:49].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:17]3[CH:16]=[C:15]([C:34]4[CH:35]=[C:36]5[C:40](=[CH:41][CH:42]=4)[C:39](=[O:43])[C:38]([OH:46])([OH:44])[C:37]5=[O:48])[CH:14]=[C:13]([C:8]4[CH:9]=[C:10]5[C:5](=[CH:6][CH:7]=4)[C:4](=[O:49])[C:3]([OH:50])([OH:2])[C:11]5=[O:12])[CH:18]=3)[CH:20]=2)[C:24]1=[O:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 59435081HCID 59435081, compound

Product 1

HCID 59435070HCID 59435070, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

1,3,5-tris(2,2-dimethoxy-1,3-dioxoindan-5-yl)benzene (26) (101 mg, 0.146 mmol) was suspended in a solvent mixture of 2 ml of acetic acid and 2 ml of water, and the suspension was mixed with 2 ml of 47% hydrobromic acid. The mixture was refluxed at 110° C. for 1.5 hours. After it was cooled to room temperature, the reaction solution was diluted with water, and the resulting solid was filtered and dried, to obtain 77.3 mg (87%) of 1,3,5-tris(2,2-dihydroxy-1,3-dioxoindan-5-yl)benzene (27) in the form of a gray solid. The readings for this compound are as follows.

Workup

  1. temperatureAfter it was cooled to room temperature
  2. filtrationthe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-a08658a8495b4f8c9868c0792f207ccd
Source dataset
uspto-grants-2012_12
Patent number
US08338028B2

Reaction notes

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