Acetic Acid → HCID 13964180, compound

HRID 625980Notes

Reaction equation

HRID 625980 reaction equation
C[O-].[Na+].CO.[C:6]([O:13][CH3:14])(=[O:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].[C:15]([O:20][CH3:21])(=[O:19])/[CH:16]=[CH:17]/[CH3:18].C(O)(=O)C.[Na+].[Cl-]>CO.O>[CH3:18][CH:17]([CH2:16][C:15]([O:20][CH3:21])=[O:19])[CH:7]([C:6]([O:13][CH3:14])=[O:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 7943Dimethyl malonateHCID 638132Methyl CrotonateHCID 23694274Sodium methanolate methanol

Product 1

HCID 13964180HCID 13964180, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 28% NaOMe/methanol (0.25 eq) and dimethyl malonate (1.0 eq) in methanol (1.6 vol) was added methyl crotonate at 70° C. The reaction mixture was stirred at the same temperature for 2 hr. After neutralization with acetic acid (0.25 eq)/water (50/50) at 25° C., the mixture was concentrated under reduced pressure. To the mixture was added 5% aq NaCl (3.82 vol) and extracted with MTBE (2 vol X 2), washed two times with 10% NaCl (2 vol) and concentrated to give the product as an oil (89.1% yield, 95% pure as measured by GC-MS).

Workup

  1. extractionextracted with MTBE (2 vol X 2)
  2. washwashed two times with 10% NaCl (2 vol)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e937386fc57f43f8adf4d65a4b5f2aed
Source dataset
uspto-grants-2016_04
Patent number
US09309204B2

Reaction notes

Loading…