Hydrochloric Acid → (2-Hydroxy-5-ethylphenyl)(5-methyl-2-thienyl)methanone

HRID 66312

Reaction equation

HRID 66312 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1.Cl>ClCC(Cl)(Cl)Cl>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([C:16]1[S:15][C:14]([CH3:13])=[CH:18][CH:17]=1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 111262-MethylthiopheneHCID 138388205-Ethyl-2-hydroxybenzoyl chloride

Product 1

HCID 13838809(2-Hydroxy-5-ethylphenyl)(5-methyl-2-thienyl)methanone

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

2-Hydroxy-5-ethylbenzoyl chloride (6.08g, 0.036 mol) and 2-methylthiophene were mixed together in tetrachloroethane (20 ml), and stannic chloride (18.78g, 0.072 mol) in tetrachloroethane (20 ml) was added dropwise with stirring, the temperature of the mixture being at about 20° C. by cooling with an ice bath. The mixture was then stirred at room temperature for 3 hours and left to stand at room temperature overnight. The resulting pink solution was poured into ice and concentrated hydrochloric acid (10 to 20 ml), stirred until the ice had melted and extracted with chloroform. The chloroform extract was washed firstly with a saturated solution of sodium bicarbonate and secondly with a saturated solution of sodium chloride, was dried (over Na2SO4), filtered and evaporated to leave an oil which distilled to give the pure title product (4.36g), bp 133°-136° C./0.1 mm, nD21 1.6341.

Workup

  1. custombeing at about 20° C.
  2. temperatureby cooling with an ice bath
  3. stirringThe mixture was then stirred at room temperature for 3 hours
  4. waitleft
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. washwas washed firstly with a saturated solution of sodium bicarbonate and secondly with a saturated solution of sodium chloride
  8. dry with materialwas dried (over Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto leave an oil which
  12. distillationdistilled

Sources & evidence

ORD record
ord-19ca998e01694300a435df813cd3cba0
Source dataset
uspto-grants-1978_12
Patent number
US04131682

Linked notes

Loading…