Hydrochloric Acid → Methyl 4-(2-methoxyethoxy)benzoate

HRID 523325Notes

Reaction equation

HRID 523325 reaction equation
[CH3:1][O:2][CH:3](O)[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.Cl>C1COCC1.O>[CH3:1][O:2][CH2:3][CH2:4][O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 30156371-Methoxyethanol

Product 1

HCID 20110213Methyl 4-(2-methoxyethoxy)benzoateYield 104.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

4.3 mL (37.5 mmol) of methoxyethanol and 10.1 g (37.5 mmol) of triphenylphosphine are added to a solution of 61 g (30 mmol) of methyl 4-hydroxybenzoate in 120 ml of THF at room temperature. 7.7 mL (37.5 mmol) of diisopropyl azodicarboxylate (DIAD) in 110 mL of THF are incorporated slowly so that the temperature is maintained to 10° C. After 18 hours at room temperature, the reaction mixture is poured onto icy water and acidified with a 1N HCl solution. The aqueous phase is extracted with ethyl acetate and the organic phase is then washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue using cyclohexane: ethyl acetate 4:1 yielded 6.6 g (98%) of pure methyl 4-(2-methoxyethoxy)benzoate as a white powder.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washthe organic phase is then washed repeatedly with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-34c0d3b6499a4e2e8b831e8c9fded0e0
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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