Hydrochloric Acid → 3-(3,4,5-Trimethoxybenzoyl)-2-propynyl 3,4,5-trimethoxybenzoate

HRID 1651839Notes

Reaction equation

HRID 1651839 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[OH:16][CH2:17][C:18]#[C:19][C:20]([C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=1)=[O:21].Cl>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([O:16][CH2:17][C:18]#[C:19][C:20](=[O:21])[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 23050496HCID 23050496, compound

Product 1

HCID 230504563-(3,4,5-Trimethoxybenzoyl)-2-propynyl 3,4,5-trimethoxybenzoate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

2.21 g (9.59 mmol) of 3,4,5-trimethoxybenzoyl chloride in 10 ml of methylene chloride and 1 ml of pyridine were o added simultaneously at 0° to a solution of 2.0 g (7.99 mmol) of 4-hydroxy-1-(3,4,5-trimethoxyphenyl)-2-butyn-1-one in 25 ml of methylene chloride. The reaction mixture was stirred at 0° for 30 minutes and at room temperature for 1.5 hours, Whereupon 30 ml of 0.5M hydrochloric acid and 100 ml of methylene chloride were added and the aqueous phase was extracted twice with methylene chloride. The combined organic phases were dried over magnesium sulphate and evaporated, and the residue was chromatographed on silica gel with ether. After recrystallization from ethyl acetate/hexane there was obtained 3-(3,4,5-trimethoxybenzoyl)-2-propynyl 3,4,5-trimethoxybenzoate of melting point 106°-108°.

Workup

  1. additionwere added
  2. extractionthe aqueous phase was extracted twice with methylene chloride
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customevaporated
  5. customthe residue was chromatographed on silica gel with ether
  6. customAfter recrystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-dfa44755c3b2467ab3068eaf15f72c96
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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