Ethylparaben → HCID 21319298, compound

HRID 262587Notes

Reaction equation

HRID 262587 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:4][CH:3]=1.O[C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1>ClCCl>[CH2:31]([O:30][C:28]([C:27]1[CH:33]=[CH:34][C:24]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]2[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:25][CH:26]=1)=[O:29])[CH3:32]

Participants

4

Reactant 2

HCID 8434EthylparabenHCID 21319301HCID 21319301, compound

Product 1

HCID 21319298HCID 21319298, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-chlorophenoxy)-13-tridecanol (3.27 g.; 0.01 M.), ethyl 4-hydroxybenzoate (2.49 g.; 0.015 M) and dicyclohexylcarbondiimide (3.09 g.; 0.015 M.) was heated at 100°-105° C. for 5 hours with stirring. The reaction mixture was cooled to room temperature, dichloromethane was added and the mixture was filtered. The filtrate was evaporated to dryness under reduced pressure and the crude product (5.95 g.) was chromatographed on silica-gel (250 g.) in dichloromethane to give 1-(4-ethoxycarbonylphenoxy)-13-(4-chlorophenoxy)-tridecane (1.82 g.; 38%). M.P. 75°-7° C.

Workup

  1. temperaturewas heated at 100°-105° C. for 5 hours
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe crude product (5.95 g.) was chromatographed on silica-gel (250 g.) in dichloromethane

Sources & evidence

ORD record
ord-e9419b193e364314ab59558c44a37c3b
Source dataset
uspto-grants-1979_05
Patent number
US04154850

Reaction notes

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