4-Methylbenzoyl Chloride → Methyl 2-(4-methylbenzoyloxy)3-propionylbenzoate

HRID 1452308Notes

Reaction equation

HRID 1452308 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[OH:11][C:12]1[C:21]([C:22](=[O:25])[CH2:23][CH3:24])=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15]>>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:11][C:12]2[C:21]([C:22](=[O:25])[CH2:23][CH3:24])=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 10899812Methyl 2-hydroxy-3-propionylbenzoate

Product 1

HCID 19972606Methyl 2-(4-methylbenzoyloxy)3-propionylbenzoate

Procedure

This compound was prepared in three steps according to the methods described for Intermediate XC (first step) and Intermediate LXXX (second and third steps). In the first step, 4-methylbenzoyl chloride was used instead of 2-furanecarbonyl chloride and methyl 2-hydroxy-3-propionylbenzoate was used instead of ethyl 2-hydroxy-3-propionylbenzoate. The reaction lasted 4 hours at room temperature, yielding methyl 2-(4-methylbenzoyloxy)3-propionylbenzoate. This compound was used without purification by column chromatography for the second step, that lasted 1.5 hours at 100° C. In the third step, 96% sulfuric acid was used instead of 37% hydrochloric acid. The title compound melted at 174°-175° C. after crystallization from ethanol.

Workup

  1. customThis compound was prepared in three steps

Sources & evidence

ORD record
ord-adcc1a91b6424da3851641b18d9791a0
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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