Hydrochloric Acid → 4-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid ethyl ester

HRID 1158468Notes

Reaction equation

HRID 1158468 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1.C([Li])CCC.CCCCCC.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].Cl>C1COCC1>[CH2:31]([O:30][C:28](=[O:29])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1)[CH3:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 10928Ethyl chloroformateHCID 615316034-Bromo-1-methoxy-2-(2-methoxy-ethoxymethyl)-benzeneHCID 178418339Butyllithium

Product 1

HCID 686167104-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-1-methoxy-2-(2-methoxy-ethoxymethyl)-benzene (2.88 g, 10.5 mmol) in absolute THF (30 mL) is added at −70° C. a 1.6N solution of n-butyllithium in hexane (7.20 mL, 11.5 mmol) with stirring. After 40 min, ethyl chloroformate (1.14 g, 10.5 mmol) is added, and the mixture is stirred overnight while gradually warming up to room temperature. The mixture is poured into 2N aqueous HCl, extracted with CH2Cl2, the organic layers are dried (Na2SO4) and concentrated. The crude product is purified by flash chromatography on silica gel (hexane/AcOEt 2:1) to give the title compound as liquid. TLC, Rf (hexane/AcOEt 1:1)=0.13.

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionextracted with CH2Cl2
  3. dry with materialthe organic layers are dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography on silica gel (hexane/AcOEt 2:1)

Sources & evidence

ORD record
ord-3670d441196e4f7d9514326461e07a9d
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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