Ethyl vinyl ether → HCID 15375046, compound

HRID 342167Notes

Reaction equation

HRID 342167 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)([CH3:23])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:9][CH:8]=1.[CH:31]([O:33][CH2:34][CH3:35])=[CH2:32].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:3]([O:4][CH:5]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH:31]([O:33][CH2:34][CH3:35])[CH3:32])=[CH:28][CH:29]=2)([CH3:23])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])=[CH:9][CH:8]=1)[CH3:1])[CH3:2]

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 6425374HCID 6425374, compound

Product 1

HCID 15375046HCID 15375046, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a solvent mixture of 75 grams of THF and 75 grams of methylene chloride was dissolved 30.9 grams (0.09 mol) of tert-butyl 4,4-bis(4'-hydroxyphenyl)valerate. With stirring, 38.9 grams (0.54 mol) of ethyl vinyl ether was added dropwise while the mixture was cooled with an ice bath so that the temperature would not exceed 10° C. After the reaction mixture was stirred for a further 20 minutes, 2.0 grams (8 mmol) of p-toluenesulfonic acid monohydrate was added and dissolved, with the mixture kept cooled so that the reaction temperature would not exceed 10° C. The ice bath was removed and the reaction mixture was stirred for 1.5 hours at room temperature. The reaction solution was cooled with ice, and 201 grams of a 0.6% sodium hydrogen carbonate aqueous solution was added to neutralize the acid for terminating the reaction. The organic layer was separated and the solvent was distilled off in vacuo, obtaining an oily product. The oily product was purified by silica gel column chromatography (eluting solvent: chloroform), isolating tert-butyl 4,4-bis(4'-(1"-ethoxyethoxy)phenyl)valerate. Amount 24.1 grams, yield 54.9%, purity 95.7%.

Workup

  1. temperaturewas cooled with an ice bath so that the temperature would not
  2. customexceed 10° C
  3. stirringAfter the reaction mixture was stirred for a further 20 minutes
  4. dissolutiondissolved, with the mixture
  5. temperaturekept cooled so that the reaction temperature would not
  6. customexceed 10° C
  7. customThe ice bath was removed
  8. stirringthe reaction mixture was stirred for 1.5 hours at room temperature
  9. temperatureThe reaction solution was cooled with ice, and 201 grams of a 0.6% sodium hydrogen carbonate aqueous solution
  10. additionwas added
  11. customfor terminating
  12. customthe reaction
  13. customThe organic layer was separated
  14. distillationthe solvent was distilled off in vacuo
  15. customobtaining an oily product
  16. customThe oily product was purified by silica gel column chromatography (eluting solvent: chloroform)

Sources & evidence

ORD record
ord-6ec2ba61d77a498aa7e2c8da20173a4a
Source dataset
uspto-grants-1999_01
Patent number
US05856561

Reaction notes

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