Acetic Acid → HCID 59132625, compound

HRID 1993026Notes

Reaction equation

HRID 1993026 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]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)=[CH:15][CH:14]=1.C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1.O>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][O:20][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[C:6]3[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]3=[O:5])=[CH:23][CH:22]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione2×HCID 41542764-[(4-methoxybenzyl)oxy]benzaldehyde

Product 1

HCID 59132625HCID 59132625, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Condensation with Meldrum's acid is carried out according to the procedure of DeWolf et al. (1989) Biochemistry 28: 3833-3842. A solution of Meldrum's acid (18 g, 124 mmol) compound 12.1 (30 g, 124 mmol) in toluene (100 mL) was treated with glacial acetic acid (4 mL) and piperidine (2 mL). The reaction mixture was stirred and heated at reflux until the removal of water with a Dean-Stark trap was complete. The reaction mixture was cooled to room temperature and the resulting solid was filtered and washed with cold toluene to yield 28 g (62%) of 12.2 as a bright yellow powder. 1H NMR (400 MHz)(DMSO-d6) δ 8.32 (s, 1H); 8.24 (d, 2H, J=8.9 Hz); 7.42 (d, 2H, J=8.6 Hz); 7.17 (d, 2H, J=9.0 Hz); 6.97 (d, 2H, J=8.7 Hz); 5.18 (s, 2H) 3.75 (s, 6H) 1.75 (s, 6H).

Workup

  1. temperatureheated
  2. filtrationthe resulting solid was filtered
  3. washwashed with cold toluene

Sources & evidence

ORD record
ord-ee60da59c3144aeca5fd258f9577aa1e
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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