Acetic Anhydride → HCID 18920664, compound

HRID 1291733Notes

Reaction equation

HRID 1291733 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:17][C:18](=[O:20])[CH3:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18920656HCID 18920656, compound

Product 1

HCID 18920664HCID 18920664, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1,2-di(p-bromophenyl)-hydroxyethane (7.2 g, 0.02 mol), acetic anhydride (20 mL, 0.2 mol), pyridine (20 mL) was stirred at 60° C. for 30 min. The solution was then allowed to stand at room temperature for 2 days. The mixture was poured into ice water (250 g) and extracted with methylene chloride (150 mL). The organic phase was extracted with 5% aqueous sodium carbonate (100 mL×2), 5% aqueous hydrochloric acid (100 mL×2), water (100 mL×2), dried over sodium sulfate and concentrated to give an oil (5.5 g) which solidified upon standing. This was purified by passing through a short alumina column followed by recrystallization from hexanes to give the above white solid product (4.2 g): mp: 61-64° C.

Workup

  1. waitto stand at room temperature for 2 days
  2. extractionextracted with methylene chloride (150 mL)
  3. extractionThe organic phase was extracted with 5% aqueous sodium carbonate (100 mL×2), 5% aqueous hydrochloric acid (100 mL×2), water (100 mL×2)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9fc0a8c112f4970a28aa3e8f47e11c4
Source dataset
uspto-grants-1998_05
Patent number
US05753757

Reaction notes

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