Water → Benzene, ((3-methyl-2-butenyl)oxy)-

HRID 263218Notes

Reaction equation

HRID 263218 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.Br[CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15]>CN(C)C=O>[O:7]([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 996PhenolHCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 564931Benzene, ((3-methyl-2-butenyl)oxy)-Yield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of phenol (18.8 g) and sodium hydroxide (8 g) was stirred at 60°-70° in dimethylformamide (162 ml) and water (18 ml) while 1-bromo-3-methylbut-2-ene (VII, R1 =R2 =CH3, Hal=Br) (29.8 g) was added dropwise over 11/2 h. The mixture was stirred at 60° for 4 h after the addition was complete. It was then poured into water (800 ml) and extracted with ether (3×300 ml). The ether extract was washed with 10% sodium hydroxide (200 ml) and then with water (3×200 ml) before drying over anhydrous sodium sulphate. The solvent was removed in vacuo, and the residue distilled to give 1-phenoxy-3-methylbut-2-ene (2.4 g, yield 75%) as a clear liquid b.p. 116°-118°/18 mm. Hg.

Workup

  1. additionafter the addition
  2. extractionextracted with ether (3×300 ml)
  3. extractionThe ether extract
  4. washwas washed with 10% sodium hydroxide (200 ml)
  5. dry with materialwith water (3×200 ml) before drying over anhydrous sodium sulphate
  6. customThe solvent was removed in vacuo
  7. distillationthe residue distilled

Sources & evidence

ORD record
ord-e536b8ddb17847838957b277ad5bf545
Source dataset
uspto-grants-1979_05
Patent number
US04156725

Reaction notes

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