Methylparaben → HCID 21997456, compound

HRID 1977258Notes

Reaction equation

HRID 1977258 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].CCCCCC>CN(C)C=O.C(OCC)(=O)C>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 8058HexaneHCID 11430Potassium CarbonateHCID 123681,6-Dibromohexane

Product 1

HCID 21997456HCID 21997456, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-hydroxybenzoic acid methyl ester (100 g) and 1,6-dibromohexane (481 g) in N,N-dimethylformamide (500 ml) was treated with potassium carbonate (109 g) then heated at 60° C. for 2 hours. After cooling, the mixture was diluted with ethyl acetate (3 L) and washed with water (7×1 L). The organic layer was dried over magnesium sulfate, filtered, and evaporated to give a crude oil. Hexane (˜100 ml) was added and the resulting precipitate removed by filtration and discarded and the filtrate loaded onto a silica gel column (2 kg). Elution with hexane, followed by 9:1 hexane-ethyl acetate and 8:1 hexane-ethyl acetate afforded methyl 4-(6-bromo-n-hexyloxy)benzoate (186 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with water (7×1 L)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a crude oil
  7. customthe resulting precipitate removed by filtration
  8. washElution with hexane

Sources & evidence

ORD record
ord-c15e3a1a371e45929e4fe3a0f2eb29e5
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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