Benzyl Chloride → 1-Phenyl-2,5,8,11-tetraoxatridecan-13-ol

HRID 895095Notes

Reaction equation

HRID 895095 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].[OH-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Na+].[Cl-]>[CH2:16]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8200Tetraethylene GlycolHCID 14798Sodium Hydroxide

Product 1

HCID 110769571-Phenyl-2,5,8,11-tetraoxatridecan-13-olYield 71%

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To the oil of monodispersed tetraethylene glycol (19.4 g, 0.10 mol) was added a solution of NaOH (4.0 g in 4.0 mL) and the reaction was sired for 15 mm. Then benzyl chloride (3.54 mL, 30.8 mmol) was added and the reaction mixture was heated to 100° C. and stirred overnight. The reaction mixture was cooled to room temperature, diluted with sat NaCl (250 mL), and washed CH2Cl2 (2×200 mL). The organic layers were combined, washed sat. NaCl, dried MgSO4, and chromatographed (silica, ethyl acetate) to afford the monodispersed compound 23 as a yellow oil (6.21 g, 71% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed CH2Cl2 (2×200 mL)
  3. washwashed sat. NaCl, dried MgSO4
  4. customchromatographed (silica, ethyl acetate)

Sources & evidence

ORD record
ord-aba6bc80cc7a435da4b242bea874482c
Source dataset
uspto-grants-2005_07
Patent number
US06913903B2

Reaction notes

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