1,2-Dichloroethane → HCID 67486722, compound

HRID 2371280Notes

Reaction equation

HRID 2371280 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH3:11][O:12][C:13](=[O:23])[C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:11][O:12][C:13](=[O:23])[C:14]1[CH:22]=[CH:21][C:17]([C:18]([CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 15513Monomethyl terephthalateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 67486722HCID 67486722, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture consisting of Meldrum's acid (2 g, 13.9 mmol), terephthalic acid monomethyl ester (2.5 g, 13.9 mmol), EDC (3.5 g, 18 mmol) and DMAP (2.2 g, 18 mmol) in DCM (50 mL) was stirred at RT overnight. The reaction mixture was diluted with DCM (to ˜100 mL) then washed with water (2×50 mL). The organic solution was dried over Na2SO4 and concentrated to afford 3.9 g of crude 4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-benzoic acid methyl ester as a yellow solid. The crude was carried on as is for the next step.

Workup

  1. washthen washed with water (2×50 mL)
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2c7613f9c6264462b4489248b7302192
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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