Acetic Acid → HCID 59435072, compound

HRID 2195600Notes

Reaction equation

HRID 2195600 reaction equation
C[O:2][C:3]1([O:34]C)[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[C:17]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[C:23](=[O:27])[C:22]([O:30]C)([O:28]C)[C:21]5=[O:32])=[CH:16][S:15][CH:14]=3)[CH:9]=2)[C:4]1=[O:33].C(O)(=O)C.Br>O>[OH:30][C:22]1([OH:28])[C:21](=[O:32])[C:20]2[C:24](=[CH:25][CH:26]=[C:18]([C:17]3[C:13]([C:8]4[CH:9]=[C:10]5[C:5](=[CH:6][CH:7]=4)[C:4](=[O:33])[C:3]([OH:34])([OH:2])[C:11]5=[O:12])=[CH:14][S:15][CH:16]=3)[CH:19]=2)[C:23]1=[O:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 59435067HCID 59435067, compound

Product 1

HCID 59435072HCID 59435072, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

3,4-bis(2,2-dimethoxy-1,3-dioxoindan-5-yl)thiophene (36) (178 mg, 0.361 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 then left all day and night to obtain a solid. The solid was filtered, washed with water, and dried, to obtain 68 mg (43%) of 3,4-bis(2,2-dihydroxy-1,3-dioxoindan-5-yl)thiophene (37) 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. waitleft all day and night
  3. customto obtain a solid
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5c4f9618e067479bb2c8e8819546aa6c
Source dataset
uspto-grants-2012_12
Patent number
US08338028B2

Reaction notes

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