Water → 4-(Chloromethyl)-1,2-bis{[2-(methyloxy)ethyl]oxy}benzene

HRID 253247Notes

Reaction equation

HRID 253247 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:17]O)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].N1C=CC=CC=1.S(Cl)([Cl:27])=O.O>O1CCCC1>[Cl:27][CH2:17][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 66891044(3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

Product 1

HCID 668895334-(Chloromethyl)-1,2-bis{[2-(methyloxy)ethyl]oxy}benzeneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (0.82 g, 3.2 mmol) and pyridine (0.41 mL 5.1 mmol) in tetrahydrofuran (20 mL) at 0° C. was added thionyl chloride (0.26 mL, 3.5 mmol) and the reaction mixture warmed to room temperature and stirred for one hour. Then it was poured into water (40 mL) and extracted with ethyl acetate (3×40 mL). The combined extract was washed with water and brine (40 mL each), dried over sodium sulfate, filtered and concentrated to give 4-(chloromethyl)-1,2-bis{[2-(methyloxy)ethyl]oxy}benzene (0.65 g, 2.4 mmol, 75% yield) 1H NMR (400 MHz, CDCl3): 6.95-6.84 (m, 3H), 4.53 (s, 2H), 4.17-4.13 (m, 4H), 3.78-3.74 (m, 4H), 3.44 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. extractionThe combined extract
  3. washwas washed with water and brine (40 mL each)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e7f018dbd9f547a69b87e53d25228846
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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