Methylparaben → HCID 2764515, compound

HRID 508417Notes

Reaction equation

HRID 508417 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18]Br>O1CCCC1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 24758Sodium hydrideHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 2764515HCID 2764515, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 4-hydroxybenzoate (366 mg, 2.41 mmol) and sodium hydride (116 mg, 60% w/w dispersion in oil, 2.65 mmol) in tetrahydrofuran (12 mL) was added 3,4-dichlorobenzyl bromide (578 mg, 2.41 mmol) and the reaction mixture was stirred at room temperature for 48 hours. The reaction was quenched by addition of methanol (15 mL) and was then evaporated to dryness. The resulting residue was purified by flash column chromatography using ethyl acetate/heptane as eluant. The title compound was isolated as a white solid (750 mg, 100%).

Workup

  1. customThe reaction was quenched by addition of methanol (15 mL)
  2. customwas then evaporated to dryness
  3. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-e94fdf6ca34f4a6e952cdfcbada04461
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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