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

HRID 2369711Notes

Reaction equation

HRID 2369711 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

Conditions

Temperature
57.5 °C

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. additionwas added
  3. extractionthe mixture extracted with ethyl acetate (2.14 L)
  4. customThe aqueous layer was separated
  5. extractionextracted twice with ethyl acetate (2.14 L, 1.28 L)
  6. washThe combined organic extracts were washed with water (2.14 L)
  7. customthen evaporated to dryness

Sources & evidence

ORD record
ord-437cd4db13c34b2ea5cde055d6c19d86
Source dataset
uspto-grants-2014_04
Patent number
USRE044874E1

Reaction notes

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