1-(Chloromethoxy)-2-methoxyethane → HCID 11470803, compound

HRID 2281624Notes

Reaction equation

HRID 2281624 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH2:22](Cl)[O:23][CH2:24][CH2:25][O:26][CH3:27]>C(Cl)Cl>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethane3×HCID 81531Diisopropylethylamine3×HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 11470803HCID 11470803, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 4-hydroxyphenylacetate (200 mg, 1.20 mmol) in DCM (5 ml) is added DIPEA (0.315 ml, 1.81 mmol), and then MEMCl (0.204 ml, 1.81 mmol), and the resulting reaction mixture is stirred for 2 hours at room temperature. An additional portion of MEMCl (0.102 ml, 1 mmol) and of DIPEA (0.158 ml, 1 mmol) are added, and the reaction mixture is stirred for a further 16 hours. An additional portion of MEMCl (0.102 ml, 1 mmol) and of DIPEA (0.158 ml, 1 mmol) are added and the reaction mixture is stirred for 3 hours. The reaction mixture is diluted with DCM and washed with 0.5 M HCl, 1 M NaOH and then 0.5 M HCl, dried (MgSO4) and concentrated in vacuo to afford [4-(2-Methoxy-ethoxymethoxy)-phenyl]-acetic acid methyl ester

Workup

  1. stirringthe reaction mixture is stirred for a further 16 hours
  2. stirringthe reaction mixture is stirred for 3 hours
  3. washwashed with 0.5 M HCl, 1 M NaOH
  4. dry with material0.5 M HCl, dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66ffcea778814c339141892a44aecca6
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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