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

HRID 723509Notes

Reaction equation

HRID 723509 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 to stand at 0° C., warming slowly to room temperature. After 36 hours 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. customto stand at 0° C.
  2. washThe mixture was then washed with 10% citric acid, water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-a99e627ffcbb4091b96a5a7985d13bef
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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