Dimethyl acetylenedicarboxylate → HCID 70605154, compound

HRID 2163400Notes

Reaction equation

HRID 2163400 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:23])[CH3:2].[C:24]([C:30]([O:32][CH3:33])=[O:31])#[C:25][C:26]([O:28][CH3:29])=[O:27].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+]>>[CH2:1]([C:3]1[C:8]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=[CH:5][C:4]=1[O:23]/[C:25](=[CH:24]\[C:30]([O:32][CH3:33])=[O:31])/[C:26]([O:28][CH3:29])=[O:27])[CH3:2]

Participants

5

Reactant 4

HCID 12980Dimethyl acetylenedicarboxylateHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 13090975HCID 13090975, compound

Product 1

HCID 70605154HCID 70605154, compound

Procedure

A mixture of 73.9 parts of 2-ethyl-3-(3-[2-propylphenoxy]propoxy)phenol, 35.0 parts of acetylene dicarboxylic acid, dimethyl ester and 4 parts of benzyl trimethyl ammonium hydroxide was warmed, with stirring, to 70° when an exothermic reaction occurred. The reaction mixture was maintained at 100°-120° for a further fifteen minutes, cooled, and 1000 parts of 1N sodium hydroxide solution was added. The mixture was extracted with chloroform and the chloroform extract washed with water and saturated sodium chloride solution and dried. Evaporation of the chloroform gave an oil which on trituration with 40/60 petrol gave a solid that crystallised from methanol to give 43.4 parts of dimethyl 2-ethyl-3-(3-[2-propylphenoxy]propoxy)phenoxy fumarate, m.pt. 63.5°-66° (raised to 71°-72.5° by recrystallisation).

Workup

  1. temperaturewas warmed
  2. customan exothermic reaction
  3. temperatureThe reaction mixture was maintained at 100°-120° for a further fifteen minutes
  4. temperaturecooled
  5. extractionThe mixture was extracted with chloroform
  6. extractionthe chloroform extract
  7. washwashed with water and saturated sodium chloride solution
  8. customdried
  9. customEvaporation of the chloroform
  10. customgave an oil which on trituration with 40/60 petrol
  11. customgave a solid
  12. customthat crystallised from methanol
  13. customto give

Sources & evidence

ORD record
ord-92a0366c5a504b5b97c3944a5eb8278f
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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