Sodium Hydroxide → HCID 18783109, compound

HRID 1420800Notes

Reaction equation

HRID 1420800 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[C:12]([CH3:16])([CH3:15])[C:13]#[CH:14].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl.O>[CH3:15][C:12]([CH3:16])([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[C:13]#[CH:14]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 18783109HCID 18783109, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

10 g (0.072 M) of 2-fluoro-4-hydroxybenzonitrile, 0.072 M of 3-chloro-3,3-dimethylpropyn and 15 g (equivalent to 16.3 ml or 0.036 M) of benzyl-trimethylammonium hydroxide (40% strength in methanol) are suspended in 80 ml of methylene chloride, a solution of 4.32 g (0.108 M) of NaOH in 80 ml of water is added, and the mixture is stirred at room temperature for 3 days. The phases are separated, and the aqueous phase is extracted several times with methylene chloride. The organic solution is washed with 10% strength NaOH and then with water and the organic solvent is distilled off under reduced pressure. 4-(1,1-Dimethyl-2-propynyloxy)-2-fluorobenzonitrile is obtained as a red-colored oily product.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted several times with methylene chloride
  3. washThe organic solution is washed with 10% strength NaOH
  4. distillationwith water and the organic solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-a4a2edf0ab6e44bf98d307f85b973233
Source dataset
uspto-grants-2000_06
Patent number
US06071953

Reaction notes

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