Methylparaben → HCID 69217139, compound

HRID 899293Notes

Reaction equation

HRID 899293 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])[CH:10]=2)[C:5]([CH3:21])([CH3:20])[CH2:4][CH2:3]1.O[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OCC)(=O)C>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[CH:32][C:23]([O:14][CH2:13][CH:12]([C:9]2[CH:10]=[C:11]3[C:6]([C:5]([CH3:20])([CH3:21])[CH2:4][CH2:3][N:2]3[CH3:1])=[CH:7][CH:8]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22640694HCID 22640694, compound

Product 1

HCID 69217139HCID 69217139, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(1,4,4-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptan-1-ol (1.2 g, 4.15 mmole) in 20 mL of THF was treated with 0.69 g of methyl 4-hydroxybenzoate, 1.2 g of triphenylphosphine and 0.72 mL of diethyl azodicarboxylate (DEAD) and heated at reflux for 6 hours. The mixture was diluted with 100 mL of ethyl acetate and washed with two 50 mL portions of water and 50 mL of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to yield 1.1 g of 4-[2-(1,4,4-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptyloxy]-benzoic acid methyl ester, as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. washwashed with two 50 mL portions of water and 50 mL of saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-296304648b114e0fbb66c985e27b6ddf
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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