Acetic Acid → 2-(4-Hydroxy-benzoyl)-cyclobutanecarboxylic acid ethyl ester

HRID 2042594Notes

Reaction equation

HRID 2042594 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([CH:9]2[CH2:12][CH2:11][CH:10]2[C:13]([OH:15])=[O:14])=[O:8])=[CH:5][CH:4]=1.Br.[C:19](O)(=O)[CH3:20]>O>[CH2:19]([O:15][C:13]([CH:10]1[CH2:11][CH2:12][CH:9]1[C:7](=[O:8])[C:6]1[CH:16]=[CH:17][C:3]([OH:2])=[CH:4][CH:5]=1)=[O:14])[CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 596519352-(4-Methoxy-benzoyl)-cyclobutanecarboxylic acid

Product 1

HCID 596519122-(4-Hydroxy-benzoyl)-cyclobutanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 2-(4-methoxy-benzoyl)-cyclobutanecarboxylic acid (10.28 g, 43.88 mmol) was added 48% hydrogen bromide in water (50 mL) and acetic acid (50 mL). After overnight stirring at 120° C., the reaction was concentrated, stirred with ethanol a few times, and the product was purified using a Single Step column (7:3 hexanes:ethyl acetate) to obtain 7.70 g (71%); MS m/z 247 (M−H)

Workup

  1. concentrationthe reaction was concentrated
  2. stirringstirred with ethanol a few times
  3. customthe product was purified
  4. customto obtain 7.70 g (71%)

Sources & evidence

ORD record
ord-8c109f440d9b424a88c112f2d65b3f71
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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