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

HRID 24993

Reaction equation

HRID 24993 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 non-polydispersed tetraethylene glycol (19.4 g, 0.10 mol) was added a solution of NaOH (4.0 in 4.0 mL) and the reaction was stirred for 15 min. 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 non-polydispersed title compound as a yellow oil (6.21 g, 71% yield).

Workup

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

Sources & evidence

ORD record
ord-34a44d5e5c3b4af0a9fd39a38db37d32
Source dataset
uspto-grants-2005_02
Patent number
US06858580B2

Linked notes

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