Methyl Vanillate → Methyl 3-Methoxy-4-[2-methyl-2-(1-pyrrolidinyl)propoxy]benzoate

Reaction equation

[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH3:14][C:15]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:18])[CH2:16]O>>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:7]=1[O:8][CH2:14][C:15]([CH3:18])([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH3:16])[C:1]([O:12][CH3:13])=[O:11]

Participants

Reactant 2

HCID 19844Methyl Vanillate

HCID 223118122-Methyl-2-(pyrrolidin-1-yl)propan-1-ol

Product 1

HCID 21182894Methyl 3-Methoxy-4-[2-methyl-2-(1-pyrrolidinyl)propoxy]benzoateYield 17%

Procedure

The title compound was prepared in 17% yield from methyl vanillate and 2-methyl-2-(1-pyrrolidinyl)propanol (Example 188, Part A) by a essentially following the procedure outlined in Example 193, Part A.

Sources & evidence

ORD record: ord-6ddb589c1cc34c49b9158701ec1212b3
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265575B1

Reaction notes

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