Methylparaben → Methyl 4-(3-chloropropoxy)benzoate

HRID 657612Notes

Reaction equation

HRID 657612 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CN(C)C=O>[Cl:22][CH2:21][CH2:20][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in example 1§E, but starting from methyl 4-hydroxybenzoate (15.2 g), potassium carbonate (65 g) and 1-bromo-3-chloropropane (50 mL) in N,N-dimethylformamide (100 mL) affords 22.5 g of methyl 4-(3-chloropropoxy)benzoate as an oil.

Sources & evidence

ORD record
ord-9554c09c5cc5439091f9820f0057af3c
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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