Methylparaben → 4-Phenethyloxybenzoic Acid Methyl Ester

HRID 970786Notes

Reaction equation

HRID 970786 reaction equation
[H-].[Na+].C1COCC1.[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.CN(C)C=O>[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 7666Phenethyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 120638344-Phenethyloxybenzoic Acid Methyl EsterYield 29.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60%) (4.400 g, 120.0 mmol) was added to freshly distilled THF chilled to 0° C., followed by 4-hydroxybenzoic acid methyl ester 9 (15.215 g, 100.0 mmol). After H2 evolution ceased, dimethylformamide (DMF) (20 ml) was added clearing the cloudy solution followed by phenethyl bromide 8 (16.39 ml, 120.0 mmol), and the mixture was stirred at 80° C. for 24 hours. Upon cooling, the mixture was poured into H2O and extracted. The organic extracts were combined, washed, dried, and evaporated. The residue was purified by chromatography to give about 7.6 g of 4-phenethyloxybenzoic acid methyl ester 10.

Workup

  1. temperatureUpon cooling
  2. extractionextracted
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-95b31d6f44ce49f48e31e078970f5722
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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