O-Cresol → Methyl 3-(4-((3-(2-methylphenoxy)benzyl)oxy)phenyl)propanoate

HRID 2422296

Reaction equation

HRID 2422296 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[O:17][C:18]1[CH:19]=[C:20]([CH2:24]O)[CH:21]=[CH:22][CH:23]=1.C1(C)C(O)=CC=CC=1.BrC1C=C(C=CC=1)C=O>>[CH3:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[O:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 335O-CresolHCID 765833-BromobenzaldehydeHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 23082899[3-(2-Methylphenoxy)phenyl]methanol

Product 1

HCID 23083053Methyl 3-(4-((3-(2-methylphenoxy)benzyl)oxy)phenyl)propanoate

Procedure

The title compound was synthesized in the same manner as in Example 277 from methyl 3-(4-hydroxyphenyl)propanoate and [3-(2-methylphenoxy)phenyl]methanol (synthesized in the same manner as in Reference Example 201 from o-cresol and 3-bromobenzaldehyde (mixture with side product)) (preparative HPLC (gradient cycle A) was used for purification). colorless oil (yield 28%).

Workup

  1. customwas used for purification)

Sources & evidence

ORD record
ord-3476422b94804a7e9a1fd304ed91910e
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Linked notes

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