Potassium Hydroxide → Bis(2-ethynylphenyl) pentanedioate

HRID 903544

Reaction equation

HRID 903544 reaction equation
[OH-:1].[K+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11].[C:12](Cl)(=[O:19])[CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>O>[C:12]([O:19][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11])(=[O:1])[CH2:13][CH2:14][CH2:15][C:16]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11])=[O:17]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 17887Pentanedioyl dichlorideHCID 1384152-Ethynylphenol

Product 1

HCID 54366211Bis(2-ethynylphenyl) pentanedioateYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500-ml., three-necked, round-bottomed flask equipped with a thermometer and mechanical stirrer was charged with a solution of potassium hydroxide, 39 g. (0.700 mole) in 360 ml. of water and then 11.7 g. (0.100 mole) of o-hydroxyphenyl acetylene (I) was added. The resulting mixture was stirred vigorously and cooled with an ice-water bath to a temperature of 10°, and then 34 g. (0.200 mole) of glutaryl chloride was added over a period of about 5 minutes. The temperature of the reaction mixture rose to 34° and subsided. After stirring at 10° C. for an additional 1.5 hours, the reaction mixture was extracted with four 200 ml-portions of ether. The combined ethereal extracts were washed with 200 ml. of 10% potassium hydroxide solution and two 200 ml-portions of water, dried, and concentrated in vacuo to give 13.0 g. (78% yield) of the desired product.

Workup

  1. custom, three-necked, round-bottomed flask equipped with a thermometer and mechanical stirrer
  2. temperaturecooled with an ice-water bath to a temperature of 10°
  3. customrose to 34°
  4. stirringAfter stirring at 10° C. for an additional 1.5 hours
  5. extractionthe reaction mixture was extracted with four 200 ml-portions of ether
  6. washThe combined ethereal extracts were washed with 200 ml
  7. dry with materialof 10% potassium hydroxide solution and two 200 ml-portions of water, dried
  8. concentrationconcentrated in vacuo
  9. customto give 13.0 g

Sources & evidence

ORD record
ord-c04b769be4794adb809a175ffb7e262f
Source dataset
uspto-grants-1980_10
Patent number
US04228126

Linked notes

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