Potassium Carbonate → HCID 54353582, compound

HRID 223768

Reaction equation

HRID 223768 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)([O:3][CH3:4])=[O:2].[Br-].[C:14]([C:18]1[CH:19]=[C:20]([CH:41]=[CH:42][CH:43]=1)[CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:21][C:20]2[CH:41]=[CH:42][CH:43]=[C:18]([C:14]([O:16][CH3:17])=[O:15])[CH:19]=2)[CH:10]=[CH:11][CH:12]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 639145Methyl 3-formylbenzoateHCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

Product 1

HCID 54353582HCID 54353582, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 49.2 g (0.3 mole) of m-carbomethoxybenzaldehyde, 221 g (0.45 mole) of m-carbomethoxybenzyl triphenyl phosphonium bromide and 1.0 g of tetrabutyl ammonium iodide in 500 ml of dichloromethane, 500 ml of 50% solution of potassium carbonate was added. The mixture was stirred at room temperature for 3 hr. The alkaline layer was separated, extracted with dichloromethane and the combined organic solvent was washed with plenty of water and dried. Evaporation of the solvent and recrystallization of the residue from ether gave 73.2 g of white needles of predominantly transisomer. Yield 82%. m.p. softens at 64° C. and melts at 105°-107° C. The infrared spectrum showed absorption at 1720 cm-1 (COOCH3), 1675 cm-1 (trans c=c), 965 cm-1 (trans c=c) and 670 cm-1 (weak cis c=c). NMR (CDCl3) showed 3.9-4.0 (d. COOCH3, 6) 67-72 (d, CH=CH, 2) and 7.3-8.4 (m, aromatic, 8). Anal. calcd. for C18H16O4 : C, 72.97%, H, 5.40. Found: C, 73.02%, H, 5.41%.

Workup

  1. additionwas added
  2. customThe alkaline layer was separated
  3. extractionextracted with dichloromethane
  4. washthe combined organic solvent was washed with plenty of water
  5. customdried
  6. customEvaporation of the solvent and recrystallization of the residue from ether

Sources & evidence

ORD record
ord-422948f4f0454b159875da2801ece371
Source dataset
uspto-grants-1982_10
Patent number
US04356292

Linked notes

Loading…