Tetrahydrofuran → 4-(2,2-Dimethyl-1-oxopropyl)benzoic acid

HRID 537496Notes

Reaction equation

HRID 537496 reaction equation
[C:1]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1COCC1.[OH-].[Na+]>CO>[C:1]([C:7]1[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:16][CH:17]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12025511ethyl 4-pivaloylbenzoate

Product 1

HCID 119589814-(2,2-Dimethyl-1-oxopropyl)benzoic acidYield 137.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A round bottom flask was charged with ethyl 4-pivaloylbenzoate (7.67 g, 32.7 mmol), THF (100 mL) and MeOH (100 mL). Sodium hydroxide 1N, aq. (65.5 mL, 65.5 mmol) was then added in one portion. Reaction stirred at 40° C. for 1 hour. Organic solvent removed under reduced pressure and water (150 mL) added to the flask. Acidification with HCl 1N aq. to ca. pH 1 followed by filtration of the solid formed over a büchner funnel provide 4-pivaloylbenzoic acid as a light yellow solid (9.25 g). 1H NMR (400 MHz, DMSO-d6) δ 1.25-1.27 (m, 9H) 7.70-7.74 (m, 2H) 7.97-8.01 (m, 2H) 13.00 (br. s., 1H); MS (M−1): 205.3.

Workup

  1. customReaction
  2. customOrganic solvent removed under reduced pressure and water (150 mL)
  3. additionadded to the flask
  4. filtrationAcidification with HCl 1N aq. to ca. pH 1 followed by filtration of the solid
  5. customformed over a büchner funnel

Sources & evidence

ORD record
ord-1fc80cf08646430f815ce297f8e32baf
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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