Hydrochloric Acid → HCID 14739661, compound

HRID 1681542Notes

Reaction equation

HRID 1681542 reaction equation
[Cl-].[C:2]([O:13][CH2:14][CH3:15])(=[O:12])[C:3]1[CH:11]=[CH:10][CH:9]=[C:5]([C:6]([O-:8])=O)[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:20]([O:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[CH2:33][C:34]#[N:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].Cl>C(Cl)Cl>[C:34]([CH2:33][C:32]1[CH:36]=[C:37]([CH:38]=[CH:39][C:31]=1[O:30][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:6]([C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[C:2]([O:13][CH2:14][CH3:15])=[O:12])=[O:8])#[N:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 151154852-(Decyloxy)benzeneacetonitrileHCID 19378217HCID 19378217, compound

Product 1

HCID 14739661HCID 14739661, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.45 g of isophthalic acid, monoethyl ester monochloride in 25 ml of methylene chloride cooled to 0° C. by means of an external ice bah were added to 2.73 g aluminum chloride. After stirring for an hour, 1.87 g of 2-decyloxybenzyl cyanide were added. The reaction was stirred at 0° C. for 4 hours and then poured into ice water containing hydrochloric acid. After stirring for 1 hour, the layers were separated. The organic layer was washed with a saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by chromatography over silica gel eluting with a 5-30% ethyl acetate in hexane gradient. The appropriate fractions were pooled and concentrated in vacuo to provide 1.1 g of the title product as a colorless oil.

Workup

  1. stirringThe reaction was stirred at 0° C. for 4 hours
  2. stirringAfter stirring for 1 hour
  3. customthe layers were separated
  4. washThe organic layer was washed with a saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography over silica gel eluting with a 5-30% ethyl acetate in hexane gradient
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04bb948e9f46472f94f461daa23277df
Source dataset
uspto-grants-1992_12
Patent number
US05171882

Reaction notes

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