4-(3,3-Dimethylcyclobutanecarbonyl)benzoic acid → Tert-butyl 4-(3,3-dimethylcyclobutanecarbonyl)benzoate

HRID 1424265Notes

Reaction equation

HRID 1424265 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:5][CH:4]([C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[O:7])[CH2:3]1>C(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH2:3][CH:4]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([O:14][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:13])=[CH:15][CH:16]=2)=[O:7])[CH2:5]1

Participants

3

Reactant 1

HCID 681574694-(3,3-Dimethylcyclobutanecarbonyl)benzoic acid

Product 1

HCID 71239401Tert-butyl 4-(3,3-dimethylcyclobutanecarbonyl)benzoateYield 113.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing 4-(3,3-dimethylcyclobutanecarbonyl)benzoic acid (1.89 g, 8.14 mmol) in anhydrous methylene chloride (20.3 mL) was added 2-tert-butyl-1,3-diisopropylurea (6.28 g, 31.3 mmol). The reaction was refluxed for 24 h. The reaction was then diluted with methylene chloride and quenched with a solution of saturated sodium bicarbonate. The aqueous layer was extracted three times with methylene chloride. The combined organic layers were washed with brine and dried with sodium sulfate, filtered, and concentrated to afford 3.09 g of a crude oil. Purification by silica gel flash chromatography (0-10% ethyl acetate in heptane) provided tert-butyl 4-(3,3-dimethylcyclobutanecarbonyl)benzoate (1.33 g, 57% yield) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.08-8.02 (m, 2H), 7.94-7.88 (m, 2H), 3.89 (quin, J=8.8 Hz, 1H), 2.24-2.16 (m, 2H), 2.11-2.02 (m, 2H), 1.62-1.59 (m, 9H), 1.27 (s, 3H), 1.08 (s, 3H). MS (M+1): 289.3.

Workup

  1. temperatureThe reaction was refluxed for 24 h
  2. customquenched with a solution of saturated sodium bicarbonate
  3. extractionThe aqueous layer was extracted three times with methylene chloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford 3.09 g of a crude oil
  9. customPurification by silica gel flash chromatography (0-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-941235b032ed4e628aad62b696937748
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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