Hydrochloric Acid → 3-Tert-butyl-5-(2-methoxyethoxy)benzoic acid

HRID 657996Notes

Reaction equation

HRID 657996 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:14]=1)[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:14]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58136955Methyl 3-tert-butyl-5-(2-methoxyethoxy)benzoate

Product 1

HCID 581368803-Tert-butyl-5-(2-methoxyethoxy)benzoic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 3-tert-butyl-5-(2-methoxyethoxy)benzoate (O5.043; 2.0 g) was dissolved in methanol (30 ml) and THF (60 ml), and lithium hydroxide solution (30 ml, 1 M in water) was added. The mixture was heated to 40° C. and stirred for 3 h. Then the organic solvents were drawn off and the aqueous phase was adjusted to pH 3 with 1 N hydrochloric acid. The mixture was extracted with EA, dried, filtered and concentrated. 1.9 g of the title compound were obtained.

Workup

  1. extractionThe mixture was extracted with EA
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbe33532df9041d9b3097689490c41cc
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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