Epichlorohydrin → 2-[[4-(2-Fluoroethoxy)phenoxy]methyl]oxirane

HRID 1774310Notes

Reaction equation

HRID 1774310 reaction equation
[OH-].[Na+].[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl.CCOC(C)=O>O>[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:16]2[CH2:17][O:18]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 150586584-(2-Fluoroethoxy)phenol

Product 1

HCID 867130932-[[4-(2-Fluoroethoxy)phenoxy]methyl]oxiraneYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of NaOH (0.35 g) in 10 mL of water was added to a mixture of 4-(2-f luoroethoxy) phenol (1.10 g, 7.1 mmol) and epichlorohydrin (0.80 mL, 10.2 mmol). The mixture was heated at 100° C. for 3 h. After cooling, the mixture is taken up with AcOEt (50 mL). The organic phase was separated, washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (Petroleum ether/AcOEt, 4:1, as eluent) to afford pure compound in 48% yield. 1H NMR (CDCl3): δ 2.60-2.70 (m, 2H), 3.16 (m, 1H), 3.89-4.04 (m, 2H), 4.17-4.28 (m, 1H), 4.50-4.65 (m, 1H), 6.54 -6.60 (m, 2H), 6.84-6.87 (m, 2H).

Workup

  1. temperatureAfter cooling
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude residue was chromatographed (Petroleum ether/AcOEt, 4:1, as eluent)
  7. customto afford pure compound in 48% yield

Sources & evidence

ORD record
ord-c8ad2e8ee1c1450c8a3355303c420a31
Source dataset
uspto-grants-2016_02
Patent number
US09260400B2

Reaction notes

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