Sodium Hydroxide → 5-tert-Butyl-isophthalic acid monomethyl ester

HRID 1640140Notes

Reaction equation

HRID 1640140 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].[OH-].[Na+]>CO.O>[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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 616620Dimethyl 5-tert-butylisophthalate

Product 1

HCID 121446585-tert-Butyl-isophthalic acid monomethyl esterYield 104.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of dimethyl 5-tert-butylisophthalate (93.3 g, 0.373 mol) in MeOH (610 mL) was added a solution of sodium hydroxide (14.9 g, 0.373 mol) in water (41 mL) at 25 ° C. The mixture was allowed to stir at this temperature for 4 h and then concentrated. The residue was suspended in 1M H2SO4 and filtered. The solid was washed with water and dried under vacuum to give 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (92 g) as a white solid which was used without purification. 1H NMR (400 MHz, d6-DMSO) δ: 8.35 (s, 1H), 8.20 (m, 2H), 3.85 (s,3H), and 1.30 (s, 9H). LCMS: ES− 235.4.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. washThe solid was washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d2b5b425d8854c2287a9d60c0a4db872
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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