Hydrochloric Acid → 4-(Cyanomethyl)-3-methoxybenzoic acid

HRID 7795

Reaction equation

HRID 7795 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[O:14][CH2:15]C)#[N:2].O.[OH-].[Li+].Cl>CO.C1COCC1.O>[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21990964Methyl 4-(cyanomethyl)-3-ethoxybenzoate

Product 1

HCID 219909984-(Cyanomethyl)-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl 4-(cyanomethyl)-3-ethoxybenzoate (18 g, 88 mmol) in 150 mL of MeOH:THF:H2O (3:3:1) was treated with lithium hydroxide monohydrate (11 g, 263 mmol) at 22° C. for overnight. Then 10% aqueous HCl (100 mL) was added to quench the reaction, the mixture was extracted with EtOAc (3×200 mL), the combined organic extracts were washed with brine (100 mL) and dried (MgSO4), filtered and concentrated in vacuo to afford 4-(cyanomethyl)-3-methoxybenzoic acid as a white solid. MS (ESI) 192 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with EtOAc (3×200 mL)
  4. washthe combined organic extracts were washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bee724b9a494d5a960226fe611b1194
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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