Acetic Anhydride → Methyl 3-formyl-3-pentylacrylate

HRID 1657212Notes

Reaction equation

HRID 1657212 reaction equation
[CH:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=O.C(OC(=O)C)(=O)C>C(O)(=O)CC.C(NCCCC)CCC>[CH:1]([C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:10][C:9]([O:13][CH3:14])=[O:12])=[O:8]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8130HeptanalHCID 70205Acetic acid, 2-oxo-, methyl ester

Product 1

HCID 53689937Methyl 3-formyl-3-pentylacrylateYield 64%

Reagents, catalysts & solvents 2

HCID 1032Propionic AcidCatalystHCID 8148DibutylamineCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 57 g (0.5 mol) of n-heptanal and 44 g (0.5 mol) of methyl glyoxylate was added dropwise to a mixture of 1.85 g (0.025 mol) of propionic acid and 3.22 g (0.025 mol) of di-n-butylamine in such a way that the temperature did not exceed 80° C. After the addition was complete the mixture was stirred at 80° C. for 30 min, then 102 g (1 mol) of acetic anhydride were added and the mixture was heated to boiling. Acetic acid slowly distilled out, 51 g being obtained in 2 hours. Fractional distillation of the bottom product yielded 59 g of methyl 3-formyl-3-pentylacrylate with a boiling point of 82°-85° C./1 mbar, corresponding to a yield of 64% of theory. The trans/cis isomer ratio was 78/22.

Workup

  1. customdid not exceed 80° C
  2. additionAfter the addition
  3. temperaturethe mixture was heated to boiling
  4. distillationAcetic acid slowly distilled out
  5. custom51 g being obtained in 2 hours
  6. distillationFractional distillation of the bottom product

Sources & evidence

ORD record
ord-938758a10d9145529389e0d5c3420bf5
Source dataset
uspto-grants-1993_10
Patent number
US05256813

Reaction notes

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