Water → 1-(1-Hydroxy-2,2,2-trichloroethyl)-2,4,5-trimethoxybenzene

HRID 1957487Notes

Reaction equation

HRID 1957487 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=[O:6].[Cl:15][C:16]([Cl:21])([Cl:20])C([O-])=O.[Na+].O>CN(C)C=O>[OH:6][CH:5]([C:4]1[CH:7]=[C:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])[C:16]([Cl:21])([Cl:20])[Cl:15]

Participants

5

Reactant 3

HCID 962WaterHCID 205252,4,5-TrimethoxybenzaldehydeHCID 23681045Sodium Trichloroacetate

Product 1

HCID 190677761-(1-Hydroxy-2,2,2-trichloroethyl)-2,4,5-trimethoxybenzeneYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 1.2 l of dimethylformamide, 196 g of 2,4,5-trimethoxybenzaldehyde were dissolved, followed by the addition of 241 g of sodium trichloroacetate salt under ice cooling. The resulting mixture was stirred at room temperature for 9 hours. After the reaction, 2 l of water were added to the reaction mixture under ice cooling. The solid so precipitated was collected by filtration, followed by washing with water and diethyl ether, whereby 272 g of 1-(1-hydroxy-2,2,2-trichloroethyl)-2,4,5-trimethoxybenzene were obtained (yield: 86%).

Workup

  1. additionwere added to the reaction mixture under ice cooling
  2. customThe solid so precipitated
  3. filtrationwas collected by filtration
  4. washby washing with water and diethyl ether

Sources & evidence

ORD record
ord-4aee7a6cc81f4e87b1d749b8934f910d
Source dataset
uspto-grants-1998_07
Patent number
US05786355

Reaction notes

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