Ethylene Glycol → HCID 13391105, compound

HRID 1153954Notes

Reaction equation

HRID 1153954 reaction equation
C(C1[CH:15]=[CH:14][CH:13]=[C:12]2[C:4]=1[CH2:5][CH2:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=12)#N.[OH-:16].[K+].[CH2:18]([OH:21])[CH2:19]O>O>[S:9]1[CH:10]=[CH:11][C:7]2[CH2:6][CH2:5][C:4]3[C:19]([C:18]([OH:21])=[O:16])=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]1=2

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 13391104HCID 13391104, compound

Product 1

HCID 13391105HCID 13391105, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 6-cyano-4,5-dihydronaphtho[1,2-b]-thiophene (4.1 g, 0.019 mole) in 75 ml of ethylene glycol, under a nitrogen atmosphere, was added potassium hydroxide [12.5 g, 0.19 mole). The reaction mixture was heated at 156°±5° for 18 hours. The cooled reaction mixture was diluted with 200 ml of cold water. The mixture was extracted with two 50 ml portions of diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid. The mixture was cooled and extracted with three 200 ml portions of diethyl ether. The extracts were combined, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give 4.4 grams of 4,5-dihydronaphtho[1,2-b]thiophen-6-carboxylic acid; mp 182°-184°.

Workup

  1. temperatureThe reaction mixture was heated at 156°±5° for 18 hours
  2. customThe cooled reaction mixture
  3. extractionThe mixture was extracted with two 50 ml portions of diethyl ether
  4. temperatureThe mixture was cooled
  5. extractionextracted with three 200 ml portions of diethyl ether
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0b1439e9f5846bf970f100f4eb5a54b
Source dataset
uspto-grants-1984_12
Patent number
US04487778

Reaction notes

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