Water → 3-[4-(4-Chlorophenoxy)phenoxy]-1-propene

HRID 1172808Notes

Reaction equation

HRID 1172808 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:18][CH:17]=[CH2:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 123461204-(4-Chlorophenoxy)phenol

Product 1

HCID 104916203-[4-(4-Chlorophenoxy)phenoxy]-1-propene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of the phenol from step 2 (16.5 g, 75 mmol), allyl bromide (10.8 g, 90 mmol) and cesium carbonate (48.7 g, 150 mmol) in DMF(300 mL) was stirred at 25° C. for 6 h. The mixture was poured into water (1.0 L) and extracted with ethyl acetate (2×200 mL). The combined organic phase was washed with water (3×100 mL), dried over magnesium sulfate and concentrated. The crude product was used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phase was washed with water (3×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0c7bb927427421f9d4f27008f71354e
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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