Ethylene Glycol → Ethanol, 2-((2,6-dichlorophenyl)methoxy)-

HRID 901627Notes

Reaction equation

HRID 901627 reaction equation
C[O-].[Na+].[CH2:4]([OH:7])[CH2:5][OH:6].[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[CH2:11]Br>O>[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[CH2:11][O:6][CH2:5][CH2:4][OH:7]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 13341669Ethanol, 2-((2,6-dichlorophenyl)methoxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium methoxide (104.4 g, 1.93 mol) was added portionwise to ethylene glycol (3.74 L) under N2, keeping the temperature below 35° C. After 1–2 h, 2,6-dichlorobenzylbromide (400 g, 1.67 mol) was added and the mixture heated to 55–60° C. for 1 h. On cooling to 20° C. water (2.14 L) was added and the mixture extracted with ethyl acetate (2.14 L). The aqueous layer was separated and extracted twice with ethyl acetate (2.14 L, 1.28 L). The combined organic extracts were washed with water (2.14 L) then evaporated to dryness to afford a colourless oil (371.8 g)—LC RT=4 min. This may be chromatographed on silica (Biotage) eluting with 10% ethyl acetate in 60/80 petrol to afford the title compound.

Workup

  1. customthe temperature below 35° C
  2. waitAfter 1–2 h
  3. temperaturethe mixture heated to 55–60° C. for 1 h
  4. additionwas added
  5. extractionthe mixture extracted with ethyl acetate (2.14 L)
  6. customThe aqueous layer was separated
  7. extractionextracted twice with ethyl acetate (2.14 L, 1.28 L)
  8. washThe combined organic extracts were washed with water (2.14 L)
  9. customthen evaporated to dryness

Sources & evidence

ORD record
ord-c764c14bc00d412e9b83b2a2b905edfa
Source dataset
uspto-grants-2008_04
Patent number
US07361787B2

Reaction notes

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