Sulfuric Acid → HCID 19423378, compound

HRID 1464180Notes

Reaction equation

HRID 1464180 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(=O)(=O)(O)O.[Cl-].[Na+].[C:32](OC(=O)C)(=[O:34])[CH3:33]>C1(C)C=CC=CC=1>[C:32]([O:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 19423376Ethyl 2-hydroxy-5-[(4-chlorosulfonylphenyl]ethynyl]benzoate

Product 1

HCID 19423378HCID 19423378, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-hydroxy-5-[(4-chlorosulfonylphenyl]ethynyl]benzoate (16 g, 44 mmol) was dissolved in acetic anhydride (40 ml) at 120° C. Sulfuric acid (about 0.4 ml) was added dropwise. After 5 min the solution was diluted with toluene (about 100 ml) and added to saturated sodium chloride solution with vigorous stirring. The phases were separated, the toluene solution dried and evaporated. More toluene was added and the evaporation repeated. The oily product crystallized. The product was sufficiently pure for the next step. Yield 17.0 g (95%).

Workup

  1. customThe phases were separated
  2. dry with materialthe toluene solution dried
  3. customevaporated
  4. additionMore toluene was added
  5. customthe evaporation
  6. customThe oily product crystallized

Sources & evidence

ORD record
ord-3421f86c48ae450daf7dddbaf4e2615d
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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