Ethylene Glycol → Poly(oxy-1,2-ethanediyl), α-[bis(4-methoxyphenyl)phenylmethyl]-ω-hydroxy-

HRID 80321Notes

Reaction equation

HRID 80321 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH3:5][O:6][C:7]1[CH:28]=[CH:27][C:10]([C:11](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:3][CH2:2][CH2:1][OH:4])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 11552316Poly(oxy-1,2-ethanediyl), α-[bis(4-methoxyphenyl)phenylmethyl]-ω-hydroxy-Yield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylene glycol (0.92 g, 14.8 mmol) (Wako Pure Chemical Industries, Ltd.), 4,4′-dimethoxytrityl chloride (1.00 g, 2.95 mmol) (Wako Pure Chemical Industries, Ltd.), and triethylamine (0.89 g, 8.81 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in methylene chloride (25 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was stirred at room temperature overnight. Water (50 mL) was added to reaction solution, and mixture was extracted with methylene chloride (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.51 g, 47% yield).

Workup

  1. extractionwas extracted with methylene chloride (Wako Pure Chemical Industries, Ltd.)
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1086c446fa6640b9ac712a4d80d3e4f9
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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