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Hydrochloric Acid → 4'-(Methoxymethyl)biphenyl-4-carboxylic acid

HRID 1519669
Notes
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Reaction equation

HRID 1519669 reaction equation
C(O)C.[OH-].[Na+].[CH3:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl>O.C1COCC1>[CH3:6][O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 71268182Ethyl 4'-(methoxymethyl)biphenyl-4-carboxylate

Product 1

HCID 712682094'-(Methoxymethyl)biphenyl-4-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Ethanol (20 mL) and a 2.0 mol/L aqueous solution (10 mL) of sodium hydroxide were added to a THF (20 mL) solution of ethyl 4′-(methoxymethyl)biphenyl-4-carboxylate (3.5 g) as obtained in Example 3-(2), and the mixture was stirred for 1 hour at 80° C. Water was added to the reaction mixture, and the mixture was neutralized with an aqueous solution of hydrochloric acid. Then, the precipitate was collected by filtration to obtain 4′-(methoxymethyl)biphenyl-4-carboxylic acid (gray solid) (3.0 g, 96%).

Workup

  1. customas obtained in Example 3-(2)
  2. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-d87fe8d4f4bc4b7a967440c6c3ec06d2
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073821B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes