Hydrochloric Acid → 3-Tert-butyl-5-(3-hydroxy-2,2-dimethylpropoxy)benzoic acid

HRID 657999Notes

Reaction equation

HRID 657999 reaction equation
C([O:4][CH2:5][C:6]([CH3:24])([CH3:23])[CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)[C:12]([O:14]C)=[O:13])(=O)C.[OH-].[Li+].Cl>CO.C1COCC1.O>[C:19]([C:17]1[CH:16]=[C:11]([CH:10]=[C:9]([O:8][CH2:7][C:6]([CH3:24])([CH3:23])[CH2:5][OH:4])[CH:18]=1)[C:12]([OH:14])=[O:13])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58046018Methyl 3-(3-acetoxy-2,2-dimethylpropoxy)-5-tert-butylbenzoate

Product 1

HCID 580458803-Tert-butyl-5-(3-hydroxy-2,2-dimethylpropoxy)benzoic acidYield 112.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 3-(3-acetoxy-2,2-dimethylpropoxy)-5-tert-butylbenzoate (O5.086; 1 g) was dissolved in methanol/THF (15/30 ml), and lithium hydroxide solution (11.89 ml, 1 M in water) was added. After stirring at 40° C. for 2 h, the organic solvent was drawn off, and the residue was diluted with water and adjusted to pH 3 with 1 N hydrochloric acid. Then it was extracted with EA, and the combined organic phases were dried, filtered and concentrated. 940 mg of the title compound were obtained. LC-MS rt: 1.45 min [M+H]+: 281.1 (met. a)

Workup

  1. extractionThen it was extracted with EA
  2. customthe combined organic phases were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-38986d28ef96453b8441f6981953c96e
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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