Methylparaben → Methyl 4-(2-(dimethylamino)ethoxy)benzoate

HRID 499188Notes

Reaction equation

HRID 499188 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 14638321Methyl 4-(2-(dimethylamino)ethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To an ice-water cooled solution of 2-dimethylamino-ethanol (305.0 mg, 3.0 mmol), 4-hydroxy-benzoic acid methyl ester (456.3 mg, 3.0 mmol), and triphenylphosphine (1.59 g, 6.0 mmol) in THF (4 mL) is added DEAD (40% solution in toluene, 2.75 mL, 6.0 mmol) dropwise. After stirred at 22° C. overnight, the reaction mixture is passed through a SGX column, washed with methanol, and eluded with 2M ammonia in methanol. Removal of the solvent gives a crude product, which is used in the next step without purification.

Workup

  1. washwashed with methanol
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-a5fb8ce8dce8489ba9c0d65035270dc1
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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