Chloromethyl Methyl Ether → HCID 59649720, compound

HRID 2081066Notes

Reaction equation

HRID 2081066 reaction equation
C(N(CC)C(C)C)(C)C.[CH2:10]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=1)[CH3:11].Cl[CH2:24][O:25][CH3:26]>ClCCl.CCOCC>[CH2:10]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([O:21][CH2:24][O:25][CH3:26])[CH:15]=1)[CH3:11]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 157454893-HYDROXY-4-METHYLBENZOIC ACID ETHYL ESTER

Product 1

HCID 59649720HCID 59649720, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (5.3 mL, 30.5 mmol) (Aldrich) was added to a suspension of ethyl 3-hydroxy-4-methylbenzoate (5.0 g, 27.75 mmol) (from Example 2 supra) in dichloromethane (20 mL) with cooling in an ice-water bath. Chloromethylmethyl ether (4.2 mL, 55.5 mmol) (Aldrich) was then added dropwise and the mixture stirred at room temperature for 5 hours. The mixture was then diluted with ether (100 mL) and washed with mixture of water (100 mL), followed by 0.1 N HCl (2×100 mL) and brine (100 mL). Aqueous layers were back washed with ether (100 mL). Organic solutions were combined, dried (MgSO4), filtered and concentrated. Residue was filtered through silica gel (Biotage 40 L) eluting with dichloromethane. Fractions were combined and concentrated to give 3-methoxymethoxy-4-methyl-benzoic acid ethyl ester as colorless oil. (Yield 4.88 g, 78.4%).

Workup

  1. temperaturewith cooling in an ice-water bath
  2. washwashed with mixture of water (100 mL)
  3. washAqueous layers were back washed with ether (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationResidue was filtered through silica gel (Biotage 40 L)
  8. washeluting with dichloromethane
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-392097b2ade443a58067cb509b7d829a
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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