Hydrochloric Acid → HCID 21412894, compound

HRID 2071223Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[C:4]([NH:10][C:11](=[O:32])[CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])=[CH:18][C:17]=2[C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH2:13][CH3:14])[C:3]=1[OH:33].[C:34]([O-])(=[O:36])[CH3:35].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)(=O)C.S(=O)(=O)(O)O.CN(C)C=O.O.CO>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:34](=[O:36])[CH3:35])[CH:5]=[C:4]([NH:10][C:11](=[O:32])[CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])=[CH:18][C:17]=2[C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH2:13][CH3:14])[C:3]=1[OH:33]

Participants

Conditions

Temperature: 80 °C

Procedure

263 g of 2-chloro-3-methyl-4-hydroxy-6-[α-(2,4-di-tert-amylphenoxy)butyramido]phenol and 5 g of sodium acetate were dissolved in 500 ml of glacial acetic acid and heated for 30 minutes at 80° C. After cooling the reaction solution, 1.5 l of water and 2 - 3 drops of concentrated sulfuric acid were added thereto and the system stirred at room temperature for 30 minutes and the diacetyl compound was deposited in the form of an oil. The oil was dissolved in 2 l of dimethylformamide and a solution of 1 l of water, 250 g of sodium carbonate and 1 l of methanol was added thereto and the system stirred at room temperature for 1 hour. 150 ml of concentrated hydrochloric acid was then added to the mixture and the mixture was poured into water and the precipitated crystals were recrystallized from methanol to obtain 212 g of the desired compound having a melting point of 188° to 190° C.

Workup

additionwere added
stirringthe system stirred at room temperature for 1 hour
customthe precipitated crystals were recrystallized from methanol

Sources & evidence

ORD record: ord-295a254430f0417e8dbb109fc369cd03
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04046573

Reaction notes

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