Lithium hydroxide, monohydrate → 5-tert-Butyl-isophthalic acid monomethyl ester

HRID 1374264Notes

Reaction equation

HRID 1374264 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15]([O:17]C)=[O:16])[CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:14]=1)[C:15]([OH:17])=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 616620Dimethyl 5-tert-butylisophthalate

Product 1

HCID 121446585-tert-Butyl-isophthalic acid monomethyl esterYield 29.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation H6, Step 1: To a solution of dimethyl 5-tert-butylisophthalate (2.5 g, 10 mmol) in 20 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (168 mg, 7 mmol) in 5.0 mL of water. The reaction mixture was stirred at RT for 3 h. THF was removed under reduced pressure to give a yellow oil which was diluted with 10 mL of 1 N HCl. The aqueous phase was extracted with EtOAc (2×25 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford 700 mg of 3-tert-butyl-5-(methoxycarbonyl)benzoic acid. MS found: (M+H)+=237.

Workup

  1. customPreparation H6, Step 1
  2. customTHF was removed under reduced pressure
  3. customto give a yellow oil which
  4. extractionThe aqueous phase was extracted with EtOAc (2×25 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7862b2ab050047f096b142da1ad19404
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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