Propiolic Acid → HCID 23050523, compound

HRID 1651847Notes

Reaction equation

HRID 1651847 reaction equation
N12CCCN=C1CCCCC2.[C:12]([OH:16])(=[O:15])[C:13]#[CH:14].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>C(Cl)Cl>[C:12]([O:16][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)(=[O:15])[C:13]#[CH:14]

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 699934-Methyloxybenzyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 23050523HCID 23050523, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

64 ml (0.43 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to a solution of 26.4 ml (0.43 mol) of propiolic acid in 400 ml of methylene chloride at 25°, where required while cooling with ice. The mixture was stirred at 25° for 2 hours, then 56 ml (415 mmol) of 4-methoxybenzyl chloride were added and the mixture was finally stirred at 25° for a further 2 days. The reaction mixture was washed in succession with 200 ml of saturated sodium hydrogen carbonate solution and twice with 200 ml of water each time. The organic phase was dried over sodium sulphate and concentrated. The residue was purified by flash chromatography on 1000 g of silica gel (elution agent hexane/ethyl acetate 9:1). There was obtained 4-methoxybenzyl propiolate as a colorless oil.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was finally stirred at 25° for a further 2 days
  3. washThe reaction mixture was washed in succession with 200 ml of saturated sodium hydrogen carbonate solution and twice with 200 ml of water each time
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on 1000 g of silica gel (elution agent hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-2a3605744d2547e8ac1eaa4b455cc964
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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