Acetic Acid → Isobutyl 2-acetyloxy-5-[2(4-sulfophenyl)ethenyl]benzoate potassium salt

HRID 743013Notes

Reaction equation

HRID 743013 reaction equation
[K:1].[K].[OH:3][C:4]1[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:13][C:5]=1[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7].[C:29](O)(=[O:31])[CH3:30].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>C(OCC)C>[K:1].[C:29]([O:3][C:4]1[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([OH:28])(=[O:26])=[O:27])=[CH:23][CH:24]=2)=[CH:13][C:5]=1[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2×HCID 86747766Isobutyl 2-hydroxy-5-[2-(4-sulfophenyl)ethenyl]benzoate dipotassium salt

Product 1

HCID 86747765Isobutyl 2-acetyloxy-5-[2(4-sulfophenyl)ethenyl]benzoate potassium salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Isobutyl 2-hydroxy-5-[2-(4-sulfophenyl)ethenyl]benzoate dipotassium salt (37.2 g, 0.09 mol) was added to a boiling solution of acetic acid (20 ml) and acetic anhydride (80ml). Sulfuric acid (8 ml) was added cautiously and the mixture refluxed until the major part of the solids had dissolved, and then more acetic anhydride (80 ml) was added. After boiling for 1 h, the mixture was cooled to room temperature. Diethyl ether (350 ml) was added and the suspension filtered and washed with diethyl ether. Yield 36.1 g (88%)

Workup

  1. temperaturethe mixture refluxed until the major part of the solids
  2. dissolutionhad dissolved
  3. filtrationthe suspension filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5707781749cb4b4c9d6939c74186559e
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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