Sodium Hydroxide → 4,5-Dichlorothiophene-2-carboxylic acid

HRID 844013Notes

Reaction equation

HRID 844013 reaction equation
[OH-:1].[Na+].ClCl.[Cl:5][C:6]1[CH:7]=[C:8]([C:12](=[O:14])C)[S:9][C:10]=1[Cl:11]>O.O1CCOCC1>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]([OH:14])=[O:1])[S:9][C:10]=1[Cl:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 1488132-Acetyl-4,5-dichlorothiophene

Product 1

HCID 3056874,5-Dichlorothiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Into a solution of sodium hydroxide (19.2 grams, 48.0 mmole) in water (30 ml) and ice (120 g) at −10° C. was bubbled Cl2 gas until 14.4 g was obtained. The solution was warmed to 50° C. and 1-(4,5-Dichloro-thiophen-2-yl)-ethanone (8.5 0 grams, 40.0 mmole) in dioxane (40 ml) was added dropwise as the temperature rose to 80-90° C. This temperature was maintained for 30 minutes. The mixture was poured into 500 ml water. This was extracted with diethyl ether, and the aqueous was treated with NaHSO3, then acidified to pH 1 with concentrated HCl. The resultant precipitate was filtered, and dried to give a white solid. (5.7 g). MW 197.04; 1H NMR (DMSO-d6) d 7.731 (1H, s).

Workup

  1. customwas obtained
  2. customrose to 80-90° C
  3. temperatureThis temperature was maintained for 30 minutes
  4. extractionThis was extracted with diethyl ether
  5. additionthe aqueous was treated with NaHSO3
  6. filtrationThe resultant precipitate was filtered
  7. customdried
  8. customto give a white solid

Sources & evidence

ORD record
ord-2eb98e649cf0456ca3ca896981fc3a81
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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