Hydrochloric Acid → HCID 21920147, compound

HRID 1592984Notes

Reaction equation

HRID 1592984 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].Cl[CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26].Cl>CN(C=O)C.C1COCC1>[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Product 1

HCID 21920147HCID 21920147, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 g (43.8 mmol) of 4′-hydroxybiphenyl-4-carboxylic acid methyl ester, 100 ml of THF and 150 ml of DMF are introduced in order and under a nitrogen stream into a 500 ml three-necked flask. 1.93 g (48.2 mmol) of NaH at 60% in oil are added in small portions and the mixture is stirred at room temperature for 15 hours. 5.75 ml of 1-chloromethoxy-2-methoxyethane are added dropwise, and the mixture is stirred at room temperature for 30 minutes. The reaction medium is poured over a 1N HCl solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulphate. After filtration and evaporation 12 g of 4′-(2-methoxyethoxymethoxy)biphenyl-4-carboxylic acid methyl ester are obtained in the form of a beige powder after filtration and evaporation (yield=87%).

Workup

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationAfter filtration and evaporation 12 g of 4′-(2-methoxyethoxymethoxy)biphenyl-4-carboxylic acid methyl ester
  6. customare obtained in the form of a beige powder
  7. filtrationafter filtration and evaporation (yield=87%)

Sources & evidence

ORD record
ord-9fdd4cbdc5c84dacbc2b3c1202671b8c
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

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