3-Tert-butyl-4-methoxybenzoyl chloride → 2-Hydroxy-4-[3-oxo-3-(3-tert-butyl-4-methoxyphenyl)-1-propynyl]benzoic acid

HRID 1275496Notes

Reaction equation

HRID 1275496 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8](Cl)=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH:16][C:17]1[CH:26]=[C:25]([C:27]#[C:28][Si](C)(C)C)[CH:24]=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20]>>[OH:16][C:17]1[CH:26]=[C:25]([C:27]#[C:28][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[CH:24]=[CH:23][C:18]=1[C:19]([OH:21])=[O:20]

Participants

3

Reactant 2

HCID 136335553-Tert-butyl-4-methoxybenzoyl chlorideHCID 22641103Methyl 2-hydroxy-4-trimethylsilylethynylbenzoate

Product 1

HCID 226194232-Hydroxy-4-[3-oxo-3-(3-tert-butyl-4-methoxyphenyl)-1-propynyl]benzoic acidYield 85.1%

Procedure

Following the basic procedure of Example 1(b), by reacting 4.2 g (0.02 mol) of 3-tert-butyl-4-methoxybenzoyl chloride with 5 g (0.02 mol) of methyl 2-hydroxy-4-trimethylsilylethynylbenzoate, 6 g (81%) of the expected compound were obtained, after purification by chromatography on a silica column eluted with dichloromethane, in the form of a brown oil.

Sources & evidence

ORD record
ord-205a21faa7214e6f8a8acf49ba46b0ea
Source dataset
uspto-grants-2000_12
Patent number
US06162445

Reaction notes

Loading…