Sulfuric Acid → HCID 23457159, compound

HRID 1680153Notes

Reaction equation

HRID 1680153 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[NH:4][C:5]1[C:6]([C:10](O)=[O:11])=[CH:7][S:8][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[NH:4][C:5]1[C:6]([CH2:10][OH:11])=[CH:7][S:8][CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3036912ClantifenHCID 21226445Aluminium lithium hydride

Product 1

HCID 23457159HCID 23457159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

57.63 g (0.2 mole) of 4-(2,6-dichloroanilino)-3-thiophencarboxylic acid (dissolved in 350 ml of tetrahydrofuran) are added dropwise to a suspension of 7.59 g (0.2 mole) of lithium aluminum hydride in 170 ml of absolute tetrahydrofuran at 15° in the course of one hour, while stirring and under nitrogen. Stirring is then continued at room temperature for one hour. The reaction mixture is hydrolyzed with 2 liters of ice-cold water, acidified to pH 5 with dilute sulfuric acid and extracted with 1.5 liters of ethyl acetate. The extract is washed with 100 ml of 2 N sodium bicarbonate solution, dried over sodium sulfate and concentrated, 4-(2,6-dichloroanilino)-3-thiophenmethanol being obtained in almost quantitative yield as a viscous oil which slowly solidifies. Recrystallization from cyclohexane gives pure 4-(2,6-dichloroanilino)-3-thiophenmethanol (m. 96° to 97°).

Workup

  1. stirringStirring
  2. extractionextracted with 1.5 liters of ethyl acetate
  3. washThe extract is washed with 100 ml of 2 N sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c27498a8f2340808d737314fff0b68d
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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