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Sodium Chloride → Ethyl 2-hydroxy-5-[(4-chlorosulfonylphenyl]ethynyl]benzoate

HRID 743020
Notes
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Reaction equation

HRID 743020 reaction equation
[K].[OH:2][C:3]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=O)=[O:23])=[CH:18][CH:17]=2)=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].CN(C)C=O.S(Cl)([Cl:33])=O.[Cl-].[Na+]>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([Cl:33])(=[O:25])=[O:23])=[CH:18][CH:17]=2)=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86747767Ethyl 2-hydroxy-5-[(4-sulfophenyl]ethynyl]benzoate potassium salt

Product 1

HCID 19423376Ethyl 2-hydroxy-5-[(4-chlorosulfonylphenyl]ethynyl]benzoate

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

Ethyl 2-hydroxy-5-[(4-sulfophenyl]ethynyl]benzoate potassium salt (19 g, 50 mmol) was suspended in toluene (100 ml). Dimethylformamide (1 ml) and thionyl chloride (12 g) were added and the suspension was refluxed for 1 h. The reaction mixture was added to a nearly saturated sodium chloride solution and the precipitated oil was extracted with toluene. The solution was dried and taken to dryness. The product was sufficiently pure for the next step. Yield 16 g, 88%.

Workup

  1. temperaturethe suspension was refluxed for 1 h
  2. extractionthe precipitated oil was extracted with toluene
  3. customThe solution was dried

Sources & evidence

ORD record
ord-e11d0483bfdb44c8988bdc7ee8a6938c
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556855

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes