Formic Acid → HCID 53880814, compound

HRID 2039425Notes

Reaction equation

HRID 2039425 reaction equation
[OH:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4].[CH:10](O)=[O:11].CNC1(NC)C=CN=CC1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCCl>[CH:10]([O:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4])=[O:11]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 10868DicyclohexylcarbodiimideHCID 953162-Propen-1-yl 2-hydroxypropanoateHCID 865890494,4-Dimethylaminopyridine

Product 1

HCID 53880814HCID 53880814, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

5.00 g (41 mmol) of 2-propenyl 2-hydroxypropionate, 2.48 g (54 mmol) of formic acid, and 1.00 g (8 mmol) of 4,4-dimethylaminopyridine (nucleating agent) were dissolved in 30 g of 1,2-dichloroethane (solvent), and a mixed solution of 12.00 g (171 mmol) of N,N′-dicyclohexylcarbodiimide (dehydrating agent) and 20 g of 1,2-dichloroethane (solvent) was added thereto at 10° C., taking 30 minutes. These were reacted at room temperature for 3 hours, the reaction liquid was filtered to remove N,N′-dicyclohexylurea, and the filtrate was concentrated. The concentrate was purified through silica gel column chromatography, and from the fraction taken with hexane/ethyl acetate=8/1, 3.5 g (yield 54%) of 2-propenyl 2-(formyloxy)propionate was obtained.

Workup

  1. customThese were reacted at room temperature for 3 hours
  2. customthe reaction liquid
  3. filtrationwas filtered
  4. customto remove N,N′-dicyclohexylurea
  5. concentrationthe filtrate was concentrated
  6. customThe concentrate was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-c67fc5efefa3452cbe79a8a77ab9e3d6
Source dataset
uspto-grants-2013_11
Patent number
US08580429B2

Reaction notes

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