Hydrochloric Acid → 3-Methyl-5-p-tolylthiophene-2-carboxylic acid

HRID 69426Notes

Reaction equation

HRID 69426 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:14]=[O:15].P([O-])(O)(O)=[O:17].[Na+].S(=O)(=O)(O)N.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([OH:17])=[O:15]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866290143-Methyl-5-p-tolylthiophene-2-carbaldehyde

Product 1

HCID 668791043-Methyl-5-p-tolylthiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-methyl-5-p-tolylthiophene-2-carbaldehyde (2.6 g) in 1,4-dioxane (30 mL) was mixed with a solution of sodium dihydrogenphosphate (5.77 g) in water, and sulfamic acid (1.87 g) was added. At 10° C., a solution of sodium chlorite (1.52 g) in water (20 mL) was added dropwise in such a way that the temperature did not rise above 10° C. Twenty minutes after the addition was complete, sodium sulfite (1.98 g) was added and the mixture was stirred for 15 minutes. The reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and concentrated. The product with the molecular weight of 232.30 (C13H12O2S) was obtained in this way; MS (ESI): 233 (M+H+).

Workup

  1. additionwas added
  2. customdid not rise above 10° C
  3. additionTwenty minutes after the addition
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customThe product with the molecular weight of 232.30 (C13H12O2S) was obtained in this way

Sources & evidence

ORD record
ord-4f1e6f4e401640a0be918906709a6af6
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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