Propofol → 2-(Chloromethoxy)-1,3-diisopropylbenzene

HRID 493055Notes

Reaction equation

HRID 493055 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].Br[CH2:15][Cl:16].[OH-].[Na+].O1CCCC1>>[Cl:16][CH2:15][O:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 4

HCID 4943PropofolHCID 6333BromochloromethaneHCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide

Product 1

HCID 112531472-(Chloromethoxy)-1,3-diisopropylbenzene

Conditions

Temperature
20 °C

Procedure

2,6-Diisopropylphenol (20 kg, FW (formula weight)=178, 112 mol, 1 equiv.) is reacted with bromochloromethane (347 kg, FW=129, 2,682 mol, 24 equiv.) and sodium hydroxide (11 kg, FW=40, 280 mol, 2.5 equiv.) in tetrahydrofuran (108 kg, FW=72, 1,498 mol, 13.3 equiv.) at reflux for approximately 1.5 hours. After cooling to 20° C., the reaction mixture is quenched with water (87 kg). The organic layer is collected and washed with 15% sodium chloride aqueous solution (78 kg) twice. The organic layer is collected again after the layer separation, and the solvents are distilled from the organic layer to afford a crude oil. The crude oil is distilled by simple distillation to yield a purified chloromethyl(2,6-diisopropylphenyl)ether (FW=227) as a light yellow oil.

Workup

  1. temperatureat reflux for approximately 1.5 hours
  2. customthe reaction mixture is quenched with water (87 kg)
  3. customThe organic layer is collected
  4. washwashed with 15% sodium chloride aqueous solution (78 kg) twice
  5. customThe organic layer is collected again
  6. customafter the layer separation
  7. distillationthe solvents are distilled from the organic layer
  8. customto afford a crude oil
  9. distillationThe crude oil is distilled by simple distillation

Sources & evidence

ORD record
ord-e106a60417a24bd2add172f42591522e
Source dataset
uspto-grants-2009_05
Patent number
US07534776B2

Reaction notes

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