Acetonitrile → Methyl 3,5-bis(methoxymethoxy)benzoate

HRID 1643691Notes

Reaction equation

HRID 1643691 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:13]([O-:16])([O-])=O.[K+].[K+].[CH2:19](Cl)[O:20][CH3:21].[CH3:23]C#N>C(Cl)Cl>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([O:1][CH2:19][O:20][CH3:21])[CH:11]=[C:10]([O:12][CH2:23][O:16][CH3:13])[CH:9]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 10106435Methyl 3,5-bis(methoxymethoxy)benzoateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 3,5-dihydroxybenzoate (250 g, 1.5 mol) and K2CO3 (500 g, 3.6 mol) in MeCN (2 L) was added drop wise MOMCl (270 g, 3.35 mol) at 0° C. The mixture was stirred at room temperature for 1.5 hr. TLC (EtOAc/petroleum ether=1/2) showed that no starting material was present. The reaction mixture was filtered and the filtrate was concentrated to give a brown oil. The oil was suspended in CH2Cl2. The resulting solid was filtered off. The filtrate was concentrated again to give the title compound (200 g, 57%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 2H), 6.91 (t, 1H), 5.19 (s, 4H), 3.90 (s, 3H), 3.47 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give a brown oil
  4. filtrationThe resulting solid was filtered off
  5. concentrationThe filtrate was concentrated again

Sources & evidence

ORD record
ord-a5f33ca0152f41f6b76942a4a340b53b
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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