Sodium Hydroxide → 2-(4-Bromophenyl)oxolane

HRID 1054870Notes

Reaction equation

HRID 1054870 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][CH2:11][O:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 146531501-(4-Bromophenyl)-4-chlorobutan-1-ol

Product 1

HCID 146531812-(4-Bromophenyl)oxolaneYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-bromophenyl)-4-chlorobutan-1-ol (1.0 g, 3.8 mmol) in tetrahydrofuran (20 mL) was added sodium hydroxide (110 mg, 4.56 mmol) at 0° C. After being stirred for 2 hours, the reaction mixture was quenched with water, brought to pH=6 with 1 M HCl aqueous, and extracted with ethyl acetate. The organic was washed with brine, dried over sodium sulfate, filtered and concentrated to give the target compound (910 mg, 100%) as a yellow solid.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f366b796115e475b914a9a1e4d73ea0c
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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