Benzoyl chloride → HCID 19108264, compound

HRID 327380Notes

Reaction equation

HRID 327380 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([I:10])[C:3]=1[OH:4].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:11]([O:4][C:3]1[C:2]([I:1])=[CH:8][C:7]([OH:9])=[CH:6][C:5]=1[I:10])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:11]([O:9][C:7]1[CH:8]=[C:2]([I:1])[C:3]([O:4][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:18])=[C:5]([I:10])[CH:6]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 747751,4-Benzenediol, 2,6-diiodo-

Product 2

HCID 19108264HCID 19108264, compoundHCID 54077011HCID 54077011, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2,6-diiodohydroquinone (0.2 g) in pyridine (10 mL) was added benzoyl chloride (0.140 mg) and the reaction mixture was stirred at room temperature for 1 hour. Following solvent removal in vacuo, purification was achieved by extraction (equal volumes ethyl acetate (EtOAc):0.01N HCl), and preparative TLC (methylene chloride) of the concentrated (in vacuo) EtOAc phases. Both the desired monoester, 4-hydroxy-2,6-diiodophenyl benzoate (Rf 0.38) and the diester, 3,5-diiodo-4(phenylmethanoyloxy)phenyl benzoate (Rf 0.96), products were formed.

Workup

  1. customFollowing solvent removal
  2. customin vacuo, purification
  3. extractionwas achieved by extraction (equal volumes ethyl acetate (EtOAc):0.01N HCl), and preparative TLC (methylene chloride) of the
  4. concentrationconcentrated (in vacuo) EtOAc phases

Sources & evidence

ORD record
ord-d9ecdf0fe41e4f7890a396d5b0c9fef3
Source dataset
uspto-grants-1993_12
Patent number
US05273885

Reaction notes

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