3-Chlorobenzoic Acid → HCID 23452403, compound

HRID 1278024Notes

Reaction equation

HRID 1278024 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[C:5](=[O:19])[CH2:6][O:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH:17]=[CH2:18])[O:10]1)[CH2:2][CH3:3].ClC1C=C(C=CC=1)C(O)=[O:28]>C(Cl)Cl>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:19])[CH2:6][O:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH:17]2[CH2:18][O:28]2)[O:10]1)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 12888747HCID 12888747, compound

Product 1

HCID 23452403HCID 23452403, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of N,N-dipropyl-2-[[tetrahydro-5-[(2-propenyloxy)methyl]-2-furanyl]methoxy]acetamide (0.016 mole) is dissolved in 300 ml of methylene chloride and 3.20 g of m-chlorobenzoic acid (1 equivalent @ 85% tech) is added at room temperature. The mixture is then stirred at 30° for 72 hours under nitrogen. The precipitated m-chlorobenzoic acid is removed via filtration. The methylene chloride mixture is then washed with 2×200 ml portions of saturated potassium carbonate solution and dried over anhydrous sodium sulfate. The methylene chloride is removed in vacuo yielding 4.86 g (92%) of the above compound as a pale yellow liquid.

Workup

  1. customThe precipitated m-chlorobenzoic acid is removed via filtration
  2. washThe methylene chloride mixture is then washed with 2×200 ml portions of saturated potassium carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe methylene chloride is removed in vacuo

Sources & evidence

ORD record
ord-d301686d8b0a46ababbbc944e1812d0b
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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