Methylparaben → 4-[2-(Morpholin-4-yl)ethoxy]benzoic acid
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:16][CH2:17]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
10 g of methyl 4-hydroxybenzoate and 20.5 g of 4-(2-chloroethyl)morpholine were dissolved in 100 ml of dimethylformamide and, after the addition of 38 g of potassium carbonate heated to 100° C. for 1 hour. The reaction mixture obtained was poured on to ice-water, extracted with ethyl acetate, dried and evaporated. The oily, slightly brown residue was saponified with potassium hydroxide in water/ethanol and, after acidification and recrystallization from hexane/ethyl acetate, gave 7.3 g of p-(2-morpholinoethoxy)benzoic acid in beige crystals, m.p. 112°-114° C.
Workup
- customThe reaction mixture obtained
- extractionextracted with ethyl acetate
- customdried
- customevaporated
- customafter acidification and recrystallization from hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-29c35e7d9c90476c9662b72a6f5a527f
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05216153
Reaction notes
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