Methylparaben → 4-[2-(4,4-Dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid methyl ester

HRID 899272Notes

Reaction equation

HRID 899272 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.O[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOCC>[CH3:29][O:28][C:26](=[O:27])[C:25]1[CH:30]=[CH:31][C:22]([O:14][CH2:13][CH:12]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([CH3:20])([CH3:1])[CH2:3][CH2:4][O:5]3)=[CH:10][CH:9]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 121490662-(4,4-Dimethyl-chroman-7-yl)-heptan-1-ol

Product 1

HCID 121490674-[2-(4,4-Dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid methyl esterYield 87.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.366 g, 1.32 mmole) in 27 mL of THF was treated with 0.222 g of methyl 4-hydroxybenzoate, 0.382 g of triphenylphosphine and 0.23 mL of diethyl azodicarboxylate (DEAD). The reaction mixture was heated at reflux for two hours, diluted with 50 mL of ether and then washed with two 25 mL portions of water and 25 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, 7% ethyl acetate in hexanes) to yield 0.474 g of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid methyl ester, as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for two hours
  3. washwashed with two 25 mL portions of water and 25 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, 7% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-dea8c0e02e8b41508f269e5eaf791656
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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