Chloroacetyl chloride → 4-Chloroacetoxystyrene

HRID 2236333Notes

Reaction equation

HRID 2236333 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12](Cl)=[O:13].CCN(CC)CC>C(OCC)C>[Cl:10][CH2:11][C:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 624534-Vinylphenol

Product 1

HCID 593017254-ChloroacetoxystyreneYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-hydroxystyrene (1.22 g, 10 mmol) in ethyl ether 140 mL was added chloroacetic chloride (2.26 g, 20 mmol) and Et3N (1.62 g, 16 mmol). After it was stirred for 2 h, the mixture was washed with brine and water. The ether solution was dried over Na2SO4 and concentrated. After purification by flash column, the 4-chloroacetoxystyrene (1.8 g, 92%) was obtained. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.46 (d, 2H, J=1.8 Hz), 7.11 (d, 2H, J=8.4 Hz), 6.73 (dd, 1H, J=17.7 Hz), 5.74 (d, 1H, J=18 Hz), 5.29 (d, J=1.1 Hz), 4.31 (s, 2H). 13C NMR (CDCl3, 75 MHz) δ 166.0, 150.0, 136.0, 135.8, 127.4, 121.3, 114.6, 41.0.

Workup

  1. washthe mixture was washed with brine and water
  2. dry with materialThe ether solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customAfter purification by flash column

Sources & evidence

ORD record
ord-150e07dccefc46f3af45231f4d2f0752
Source dataset
uspto-grants-2010_05
Patent number
US07714161B2

Reaction notes

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