Water → 4-[(4-Ethenylphenyl)methoxy]butan-1-OL

HRID 2230229Notes

Reaction equation

HRID 2230229 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].C1O[CH2:23][CH2:22]OCCOCCOCCOCCOC1.O.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[OH:5][CH2:4][CH2:3][CH2:2][CH2:1][O:6][CH2:32][C:26]1[CH:31]=[CH:30][C:29]([CH:22]=[CH2:23])=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 80641,4-ButanediolHCID 2855718-Crown-6

Product 1

HCID 184655334-[(4-Ethenylphenyl)methoxy]butan-1-OL

Procedure

1,4-Butanediol (50.00 g) was dissolved in dry toluene (60 ml), para-choloromethylstyrene (15.62 g; 0.1 mol) was then added with stirring. A catalytic quantity of 18-crown-6 (0.3 g) was then added. The flask was stoppered, stirred at room temperature for 18 hours and for a further 4 hours at 45-60°. The resulting solution was then poured in to water (500 ml) and extracted with dichloromethane (3×75 ml). The combined extracts were dried (MgSO4) and evaporated (20°/21 mm) to give a yellow oil, which was distilled to give a yellow oil (14.33 g; 69.6%).b.pt. 152-157°/1 mbar.

Workup

  1. additionpara-choloromethylstyrene (15.62 g; 0.1 mol) was then added
  2. stirringstirred at room temperature for 18 hours and for a further 4 hours at 45-60°
  3. extractionextracted with dichloromethane (3×75 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated (20°/21 mm)
  6. customto give a yellow oil, which
  7. distillationwas distilled
  8. customto give a yellow oil (14.33 g; 69.6%)

Sources & evidence

ORD record
ord-677a26f99a654b2c97654e0f6afc23a6
Source dataset
uspto-grants-2002_07
Patent number
US06423761B1

Reaction notes

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