Methylparaben → Methyl 4-{10-(1,8-nonadien-5-yloxy)decyloxy}benzoate

HRID 1755612Notes

Reaction equation

HRID 1755612 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:13]([CH2:18][CH2:19][CH:20]=[CH2:21])[CH2:14][CH2:15][CH:16]=[CH2:17].[OH:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:17]=[CH:16][CH2:15][CH2:14][CH:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=1)[CH2:18][CH2:19][CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 199176565-(10-Bromodecyloxy)-1,8-nonadiene

Product 1

HCID 19917652Methyl 4-{10-(1,8-nonadien-5-yloxy)decyloxy}benzoateYield 64%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3 g of the compound (7), 1.5 g of methyl 4-hydroxybenzoate and 4.1 g of potassium carbonate were dissolved in 50 ml of 2-butanone, and reflux was carried out for 10 hours in an atmosphere of argon. After the precipitated solid matter was filtered off, the solvent was evaporated, and the residue was purified by a chromatography using a column filled with alumina and silica gel, to obtain 2.3 g of the compound (8). (Yield: 64%)

Workup

  1. temperaturereflux
  2. filtrationAfter the precipitated solid matter was filtered off
  3. customthe solvent was evaporated
  4. customthe residue was purified by a chromatography
  5. additionfilled with alumina and silica gel

Sources & evidence

ORD record
ord-3e94d3d98e4548a4a88777f2385f9176
Source dataset
uspto-grants-1995_08
Patent number
US05437816

Reaction notes

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