Methanol → HCID 68153231, compound

HRID 1405411Notes

Reaction equation

HRID 1405411 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[C:13][CH2:14][O:15][CH3:16])[C:5]([O:7]C)=[O:6].CO.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[C:13][CH2:14][O:15][CH3:16])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68153367Methyl 3-fluoro-4-(3-methoxyprop-1-ynyl)benzoate

Product 1

HCID 68153231HCID 68153231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3-fluoro-4-(3-methoxyprop-1-ynyl)benzoate (1.40 g, 6.30 mmol) in 15 ml of 2:1 THF:MeOH at room temperature was added NaOH (1.89 mL of 4 M, 7.56 mmol). The mixture was stirred at room temperature for 1 h before the volatile solvents were removed. The remainder was extracted with ether. The aqueous layer was acidified with 1M HCl and was extracted with ether (3×). The combined ether extracts were dried and concentrated to give 3-fluoro-4-(3-methoxyprop-1-ynyl)benzoic acid as a white solid. ESI-MS m/z calc. 208.2, found 209.2 (M+1)+; Retention time: 1.22 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.85 (dd, J=8.0, 1.4 Hz, 1H), 7.80 (dd, J=9.5, 1.3 Hz, 1H), 7.59-7.49 (m, 1H), 4.39 (s, 2H), 3.48 (s, 3H).

Workup

  1. customwere removed
  2. extractionThe remainder was extracted with ether
  3. extractionwas extracted with ether (3×)
  4. dry with materialThe combined ether extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6f9a7495df8455ab8fd63a0754a446a
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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