Chloromethyl Methyl Ether → Methyl 3-hydroxy-5-(methoxymethoxy)benzoate

HRID 1678592Notes

Reaction equation

HRID 1678592 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N(CC)C(C)C)(C)C.Cl[CH2:23][O:24][CH3:25]>ClCCl>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:23][O:24][CH3:25])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 75076Methyl 3,5-DihydroxybenzoateHCID 81531Diisopropylethylamine

Product 1

HCID 23136427Methyl 3-hydroxy-5-(methoxymethoxy)benzoateYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With ice cooling, to a solution of methyl 3,5-dihydroxybenzoate (14.0 g, 83.3 mmol) and N,N-diisopropylethylamine (11.0 g, 85.0 mmol) in dichloromethane (100 mL) was added dropwise chloromethylmethyl ether (6.84 g, 85.0 mmol), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with dichloromethane (300 mL), and the organic layer was washed successively with a 3% aqueous hydrochloric acid solution, a saturated aqueous sodium bicarbonate solution and saturated brine, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=4:6) to give the title compound (7.74 g, yield 44%) as an oily matter.

Workup

  1. washthe organic layer was washed successively with a 3% aqueous hydrochloric acid solution
  2. concentrationa saturated aqueous sodium bicarbonate solution and saturated brine, and then concentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=4:6)

Sources & evidence

ORD record
ord-715f440a68424b87829c114cc7024063
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

Loading…