Chloromethyl Methyl Ether → Ethyl 2-methoxymethoxy-6-methylbenzoic acid

HRID 493127Notes

Reaction equation

HRID 493127 reaction equation
[CH2:1]([C:3]1[C:4]([OH:13])=[C:5]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:23][O:24][CH2:25]Cl>ClCCl>[CH2:1]([C:3]1[C:4]([O:13][CH2:23][O:24][CH3:25])=[C:5]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 302342,6-Cresotic acid, 3-ethyl-HCID 81531Diisopropylethylamine

Product 1

HCID 21873652Ethyl 2-methoxymethoxy-6-methylbenzoic acidYield 111.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-hydroxy-6-methylbenzoic acid (4.56 g, 25.3 mmol) and diisopropylethylamine (13.2 ml, 76 mmol) in dry dichloromethane (30 ml) was cooled in an ice-bath. Chloromethyl methyl ether (3.83 ml, 50.6 mmol) was added slowly and the mixture was allowed stand at 0° C., warning slowly to room temperature. After 36 h a further portion of chloromethyl methyl ether (1.9 ml) was added and the mixture was left at room temperature overnight. The mixture was then washed with 10% citric acid, water and brine, dried and evaporated to give the title compound (6.34 g, 100%).

Workup

  1. customat 0° C.
  2. customwarning slowly to room temperature
  3. washThe mixture was then washed with 10% citric acid, water and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-74e5c891364c4b4c9302227404e65486
Source dataset
uspto-grants-2009_05
Patent number
US07534793B2

Reaction notes

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