Sodium Hydroxide → 2-(3-Fluorophenyl)cyclopropanecarboxylic acid

HRID 2069184Notes

Reaction equation

HRID 2069184 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13]C)=[O:12])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][CH:9]2[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59414891Methyl 2-(3-fluorophenyl)cyclopropanecarboxylate

Product 1

HCID 218646592-(3-Fluorophenyl)cyclopropanecarboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7 (390 mg, 2.0 mmol) in MeOH (5 mL) was added 2N NaOH (5 mL) slowly. The reaction solution was stirred at room temperature for 2 h then diluted with H2O (25 mL). After extraction with ether (20 mL), the aqueous layer was acidified with 2N HCl (2.1 mL). The resulting solution was extracted with ether (3×40 mL). The combined organic layers were dried over MgSO4 and concentrated to give 8 (325 mg, 1.8 mmol, 99%) as a light yellow oil: 1H NMR (500 MHz, CDCl3) δ 0.87-0.91 (dd, J=6.0, 13.5 Hz, 1H), 1.21-1.29 (m, 1H), 1.39-1.43 (ddd, J=5.0, 6.5, 8.0 Hz, 1H), 1.67-1.72 (m, 1H), 1.90-1.94 (m, 1H), 2.58-2.63 (m, 1H), 6.79-6.82 (dd, J=2.0, 5.5 Hz, 1H), 6.90-6.95 (m, 2H), 7.24-7.28 (m, 1H), 8.90-11.00 (br s, 1H); 13C NMR (125 MHz, CDCl3) δ 17.8, 24.4, 26.9, 31.8, 113.3, 113.5, 113.8, 114.0, 122.30, 122.32, 130.2, 130.3, 142.4, 142.5, 162.2, 164.2, 179.8; LCQ-MS (M−H+) calcd for C10H8FO2 179. found 179.

Workup

  1. extractionAfter extraction with ether (20 mL)
  2. extractionThe resulting solution was extracted with ether (3×40 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09e28c666710459688570a6acb97b115
Source dataset
uspto-grants-2012_10
Patent number
US08299100B2

Reaction notes

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