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ChemicalBook CAS DataBase List Dimethyl adipate
627-93-0

Dimethyl adipate synthesis

10synthesis methods
Dimethyl adipate was synthesized by immobilized Candida antarctica lipase B-catalyzed esterification of adipic acid and methanol.
Synthesis of Diethyl Adipate
According to the general procedure described above, Dimethyl adipate has been synthesized from adipic acid (730mg, 5 mmol) and methanol (10 ml). Yield: 9%.
1H NMR (400.1 MHz, CDCl3): δ = 3.56 (6H, s, H1-H10), 2.23 (4H, m, H4-H7), 1.56 (4H, m, H5-H6).
13C NMR (100.5 MHz, CDCl3): δ = 173.4 (C3-C8), 51.2 (C1-C10), 33.4 (C4-C7), 24.1 (C5-C6)
https://pubmed.ncbi.nlm.nih.gov/20632329/
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Yield:627-93-0 73%

Reaction Conditions:

with triethylamine at 160; for 5 h;Autoclave;Green chemistry;

Steps:

Methylation of carboxylic acids with dimethylcarbonate. General procedure
General procedure: Into a stainless steel pressure microreactor of capacity 17 mL was charged 5 wt % of zeolite NaY-Bf, 100 mmol of carboxylic acid, and 300-400 mmol of dimethyl carbonate, the reactor was hermetically closed, and the reaction mixture was heated at 180-200°C for 5 h. On completion of the reaction the reactor was cooled to room temperature, opened, the reaction mixture was filtered through a bed of Al2O3. Unreacted dimethyl carbonate was distilled off, the residue was distilled at atmospheric pressure or in a vacuum, or it was crystallized from ethanol.

References:

Khusnutdinov;Shchadneva;Mayakova, Yu. Yu.;Konovalova, Yu. S.;Khazipova;Kutepov [Russian Journal of Organic Chemistry,2017,vol. 53,# 2,p. 163 - 168][Zh. Org. Khim.,2017,vol. 53,# 2,p. 177 - 181,5]

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