Sodium hydride → 1-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid

HRID 2354943Notes

Reaction equation

HRID 2354943 reaction equation
C[O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[H][H].Br[CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]>CN(C=O)C>[CH2:23]([O:22][CH:21]([O:25][CH2:26][CH3:27])[CH2:20][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2([C:3]([OH:2])=[O:4])[CH2:7][CH2:6]2)=[CH:9][CH:10]=1)[CH3:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 20770793Methyl 1-(4-hydroxyphenyl)cyclopropane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 591292871-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acidYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a stirred solution of 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (15.0 g, 84.3 mmol) in DMF (50 mL) was added sodium hydride (6.7 g, 170 mmol, 60% in mineral oil) at 0° C. After hydrogen evolution ceased, 2-bromo-1,1-diethoxy-ethane (16.5 g, 84.3 mmol) was added drop-wise to the reaction mixture. The reaction was stirred at 160° C. for 15 hours. The reaction mixture was poured onto ice (100 g) and extracted with dichloromethane. The combined organics were dried over Na2SO4. The solvent was evaporated under vacuum to give crude 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (10 g), which was used directly in the next step without purification.

Workup

  1. additionThe reaction mixture was poured onto ice (100 g)
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organics were dried over Na2SO4
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-5660b6697254496391c99d1e0bf8e173
Source dataset
uspto-grants-2010_07
Patent number
US07754739B2

Reaction notes

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