Hydrochloric Acid → HCID 54340804, compound

HRID 1584253Notes

Reaction equation

HRID 1584253 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)O)=[CH:5][CH:4]=1.[N+:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([O-:21])=[O:20].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[CH:22]([N+:19]([O-:21])=[O:20])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69379Ethyl nitroacetateHCID 69768p,p'-Dimethoxybenzhydryl alcoholHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54340804HCID 54340804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred (0° C.) solution of bis-(4-methoxyphenyl)methanol (2.5 g, 10.2 mmol) and ethyl nitroacetate (2.26 ml, 20.4 mmol) in CH2Cl2 (50 ml) under argon was added AlCl3 (1.36 g, 10.2 mmol) in one portion. After 1 h, the reaction mixture was allowed to warm to approximately 10° C. and poured into a mixture of ice and 2M HCl. The resulting mixture was stirred for 45 min, and the aqueous layer extracted with CH2Cl2. The combined organic layers were washed with 10% Na2CO3, dried over MgSO4, treated with activated carbon, and concentrated to give a reddish oil that was chromatographed (CHCl3 elution) to afford the title compound as a colorless oil.

Workup

  1. extractionthe aqueous layer extracted with CH2Cl2
  2. washThe combined organic layers were washed with 10% Na2CO3
  3. dry with materialdried over MgSO4
  4. additiontreated with activated carbon
  5. concentrationconcentrated
  6. customto give a reddish oil that
  7. customwas chromatographed
  8. wash(CHCl3 elution)

Sources & evidence

ORD record
ord-57209f260db542a89ff222b9dcdf3398
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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