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

HRID 401532

Reaction equation

HRID 401532 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 dropwise 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 CH2Cl2. 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 CH2Cl2
  3. dry with materialThe combined organics were dried over Na2SO4
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-2f736a7df2e24863bafe9caa317e3f49
Source dataset
uspto-grants-2014_06
Patent number
US08741933B2

Linked notes

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