Chloromethyl Methyl Ether → HCID 117701621, compound

HRID 1507431Notes

Reaction equation

HRID 1507431 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:13])[CH2:11][CH3:12].C(N(C(C)C)CC)(C)C.Cl[CH2:24][O:25][CH3:26]>ClCCl>[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:24][O:25][CH3:26])[CH:5]=[CH:4][C:3]=1[C:10](=[O:13])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 5921571-(2,4-Dihydroxy-3-methylphenyl)propan-1-one

Product 1

HCID 117701621HCID 117701621, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture composed of 1-(2,4-dihydroxy-3-methylphenyl)propan-1-one (5.00 g, 27.8 mmol) and dichloromethane (80 mL), diisopropylethylamine (5.26 mL, 30.5 mmol) was added under cooling with ice, and then a solution of chloro(methoxy)methane (2.30 mL, 30.5 mmol) in dichloromethane (20 mL) was added dropwise to the mixture over 20 minutes. After the completion of dropwise addition, the mixture was brought back to room temperature and stirred overnight. Dichloromethane was added to the reaction solution. The organic layer was washed with water and then dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=90/10→70/30) to obtain 5.73 g of the title compound (yield: 92%).

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. additionAfter the completion of dropwise addition
  4. customwas brought back to room temperature
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=90/10→70/30)

Sources & evidence

ORD record
ord-d77bfbe76481459f9a21fdf53d9e9078
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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