Chloromethyl Methyl Ether → HCID 22715031, compound

HRID 352030Notes

Reaction equation

HRID 352030 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[OH:14])([CH3:6])([CH3:5])[CH3:4].[CH2:15](Cl)[O:16][CH3:17].[Cl-].[NH4+]>CCCCCC.C1COCC1.C(OCC)(=O)C>[C:3]([C:7]1[C:8]([O:14][CH2:15][O:16][CH3:17])=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

8

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 166782-tert-Butyl-6-methylphenolHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 22715031HCID 22715031, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (60% in mineral oil, 4.5 g, 0.12 mol) is washed twice with hexane (50 ml) and added with THF (75 ml), and the mixture was cooled to below 10° C. A solution of 2-tert-butyl-6-methylphenol 42 (16.4 g, 0.1 mol) in THF (60 ml) was then dropwise and slowly added, and the mixture was stirred for 10 minutes under the same conditions. The mixture was then dropwise added with MOMCl (9.1 ml, 0.12 mol), warmed to room temperature, and the reaction mixture was added with saturated aqueous ammonium chloride (200 ml) and ethyl acetate (200 ml). The organic layer was separated, washed sequentially with water (200 ml), 1.5N NaOH (200 ml), water (100 ml), and saturated brine (200 ml), and dried. The solvent was removed in vacuo to give 20.5 g (98.6%) of 43 as colorless oil.

Workup

  1. temperaturethe mixture was cooled to below 10° C
  2. additiondropwise and slowly added
  3. customThe organic layer was separated
  4. washwashed sequentially with water (200 ml), 1.5N NaOH (200 ml), water (100 ml), and saturated brine (200 ml)
  5. customdried
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d720a00080cb42239639a09459ae4517
Source dataset
uspto-grants-2004_06
Patent number
US06743923B2

Reaction notes

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