Tetrahydrofuran → 4-(3,3-Dimethylcyclobutanecarbonyl)benzoic acid

HRID 1424264Notes

Reaction equation

HRID 1424264 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:5][CH:4]([C:6]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)=[O:7])[CH2:3]1.O1CCCC1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:19])[CH2:3][CH:4]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:17][CH:18]=2)=[O:7])[CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68157422Ethyl 4-(3,3-dimethylcyclobutanecarbonyl)benzoate

Product 1

HCID 681574694-(3,3-Dimethylcyclobutanecarbonyl)benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing ethyl 4-(3,3-dimethylcyclobutanecarbonyl)benzoate (3.00 g, 12.0 mmol) was added anhydrous tetrahydrofuran (28.8 mL), methanol (28.8 mL), and 1 N sodium hydroxide (28.8 mL, 28.8 mmol). After 1 h, the reaction was concentrated to a white solid. The solid was the redissolved in 700 mL of water. With vigorous stirring, 1 N HCl (29.0 mL) was added dropwise and the suspension was stirred for 30 min. at room temperature. The solid was then collected with a Buchner funnel and the solid was washed two times with water. The solid was then azeotrophed with toluene to give 4-(3,3-dimethylcyclobutanecarbonyl)benzoic acid (2.15 g, 92% yield) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.21-8.15 (m, 2H), 8.01-7.94 (m, 2H), 3.91 (quin, J=8.9 Hz, 1H), 2.28-2.17 (m, 2H), 2.15-2.04 (m, 2H), 1.28 (s, 3H), 1.09 (s, 3H). MS (M-1): 231.4.

Workup

  1. concentrationthe reaction was concentrated to a white solid
  2. dissolutionredissolved in 700 mL of water
  3. additionWith vigorous stirring, 1 N HCl (29.0 mL) was added dropwise
  4. customThe solid was then collected with a Buchner funnel
  5. washthe solid was washed two times with water

Sources & evidence

ORD record
ord-436c7e2364934612baf50e00ed428c3f
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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