Methylparaben → HCID 43532221, compound

HRID 552572Notes

Reaction equation

HRID 552572 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.[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/[N:43]=N/C(OCC)=O)=O>C1COCC1>[NH3:43].[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][Cl:12])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 789155-Chloro-1-pentanolHCID 5462977Diethyl azodicarboxylate

Product 2

HCID 222AmmoniaHCID 43532221HCID 43532221, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxy-benzoic acid methyl ester (1.52 g, 10 mmol), 5-chloro-1-pentanol (1.22 g, 10 mmol) and triphenylphosphine (2.62 g, 10 mmol) are dissolved in dry THF (30 mL) and cooled to 0° C. Diethylazodicarboxylate (DEAD) (1.74 g, 10 mmol) is dropped into this mixture at 0° C. and stirred at room temperature for 3 days. The reaction mixture is washed with brine, dried over Na2SO4, filtered and evaporated. The crude product is purified using silica-gel column chromatography (CH2Cl2 only to CH2Cl2:2 M NH3 in MeOH=20:1) to give the desired product (1.14 g, 45%). NMR (CDCl3): δ 7.98 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.8 Hz), 4.02 (t, 2H, J=6.5 Hz), 3.88 (s, 3H), 3.57 (t, 2H, J=6.7 Hz), 1.85 (m, 4H), 1.64 (m, 2H).

Workup

  1. washThe reaction mixture is washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified

Sources & evidence

ORD record
ord-1635b69b39964172a09a370041b33c90
Source dataset
uspto-grants-2011_05
Patent number
US07951826B2

Reaction notes

Loading…