Di-p-tolylhydroxyacetic acid methyl ester → Tropenol 4,4'-dimethylbenzilate

HRID 1994223Notes

Reaction equation

HRID 1994223 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)([OH:11])[C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[C@@:21]12(O)[N:28](C)[C@@H:25]([CH2:26][CH2:27]1)[CH2:24][CH:23]=[CH:22]2>>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:20][CH:19]=2)([OH:11])[C:7]([O:9][C@@:10]23[N:28]([CH3:21])[C@@H:25]([CH2:26][CH2:27]2)[CH2:24][CH:23]=[CH:22]3)=[O:8])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 22574226Di-p-tolylhydroxyacetic acid methyl esterHCID 53629842Tropenol

Product 1

HCID 86761046Tropenol 4,4'-dimethylbenzilate

Procedure

4.10 is prepared analogously to the method according to II.1. Yield: 3.55 g (81% of theory) starting from 2.87 g (0.01 mol) of 3e and 1.48 g (0.01 mol) of tropenol; to purify it, the hydrochloride was precipitated and recrystallized from acetonitrile. Melting point: 232° C.-233° C. (hydrochloride).

Workup

  1. custom4.10 is prepared analogously to the method
  2. customto purify it
  3. customthe hydrochloride was precipitated
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f1d07881b7fc4bb4b5ca899b4c3bace9
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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