4-Methoxybenzoic Acid → HCID 57422612, compound

HRID 493366Notes

Reaction equation

HRID 493366 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.[Br:24][CH2:25][CH2:26][CH2:27]O>CN(C)C1C=CN=CC=1.ClCCl>[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:21][CH2:27][CH2:26][CH2:25][Br:24])=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 74784-Methoxybenzoic AcidHCID 123083-Bromo-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57422612HCID 57422612, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC) (3.4 g, 17.7 mmol) was slowly added to a solution of 4-methoxybenzoic acid (2.0 g, 13.1 mmol), 3-bromopropan-1-ol (1.1 mL, 12.6 mmol), and 4-(dimethylamino)pyridine (100 mg) in 80 mL of anhydrous dichloromethane. The mixture was stirred at room temperature for 16 hrs. The reaction mixture was diluted with dichloromethane and washed with 0.5N HCl twice, followed by the addition of saturated NaHCO3 solution and brine. The organic layer was dried through MgSO4 and concentrated under reduced pressure. Chromatography (silica gel, 1:10 ethyl acetate/hexane) of the residue afforded 2.1 g (61%) of 3-Bromopropyl 4-methoxybenzoate.

Workup

  1. washwashed with 0.5N HCl twice
  2. additionfollowed by the addition of saturated NaHCO3 solution and brine
  3. dry with materialThe organic layer was dried through MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46b0394d52014209ab31ddcfed3e91a8
Source dataset
uspto-grants-2009_05
Patent number
US07534813B2

Reaction notes

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