Hydrochloric Acid → (2E)-3-(4-Bromo-2-thienyl)-2-propenoic acid

HRID 1073241Notes

Reaction equation

HRID 1073241 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[Br:8][C:9]1[CH:10]=[C:11](C=O)[S:12][CH:13]=1.[OH-].[K+].Cl>N1C=CC=CC=1.N1CCCCC1.O>[Br:8][C:9]1[CH:10]=[C:11](/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])[S:12][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 14797Potassium HydroxideHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 5708462(2E)-3-(4-Bromo-2-thienyl)-2-propenoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8082PiperidineSolvent

Conditions

Temperature
100 °C

Procedure

Malonic acid (16.2 g) was added to a solution of 4-bromothiophen-2-aldehyde (25.1 g) in pyridine (100 cm3) and piperidine (3.2 cm3) and the resulting mixture was heated at 100° C. for 6.5 hours, allowed to cool to room temperature overnight and was then evaporated down to give a beige semi-solid. The semi-solid was treated with aqueous potassium hydroxide solution and the resulting mixture was diluted with water (50 cm3), acidified with concentrated hydrochloric acid (90 cm3) and then cooled to yield a precipitate which was filtered off, washed with ether/40-60 petrol and was then sucked dry (26.1 g) m.p. 167°-169° C. (aqueous methanol) Analysis; Calculated; C, 36.05; H, 2.15; Found; C, 36.30; H, 2.03.

Workup

  1. temperatureto cool to room temperature overnight
  2. customwas then evaporated down
  3. customto give a beige semi-solid
  4. temperaturecooled
  5. customto yield a precipitate which
  6. filtrationwas filtered off
  7. washwashed with ether/40-60 petrol
  8. dry with materialwas then sucked dry (26.1 g) m.p. 167°-169° C. (aqueous methanol) Analysis

Sources & evidence

ORD record
ord-24cb66f7b3f1437c91a6a0be21a60dec
Source dataset
uspto-grants-1990_11
Patent number
US04968698

Reaction notes

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