1-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochloride → 4-Chlorotoluene

HRID 1156670Notes

Reaction equation

HRID 1156670 reaction equation
[ClH:1].[C:2]([NH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)=[O:9])([CH3:5])([CH3:4])[CH3:3].[CH3:18][O-].[Na+].[C:21]1([O-])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+]>CN(C)C=O>[C:10]1([CH3:8])[CH:15]=[CH:14][C:13]([Cl:1])=[CH:12][CH:11]=1.[C:2]([NH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:24]2[CH:25]=[CH:26][C:21]([CH3:18])=[CH:22][CH:23]=2)=[C:12]([OH:17])[CH:11]=1)=[O:9])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 30157041-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochlorideHCID 4445035Phenolate SodiumHCID 10942334Sodium Methoxide

Product 2

HCID 78104-ChlorotolueneHCID 541899733-Hydroxy-4-(p-toluyloxy)phenyl tert-butylaminomethyl ketone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following a procedure similar to that described in Example 58A above, 13 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride was reacted with 8.1 g. of sodium methoxide in 200 ml. of N,N-dimethylformamide, and the resulting sodium phenolate was interacted with 8.5 g. of p-toluyl chloride to yield 3-hydroxy-4-(p-toluyloxy)phenyl tert-butylaminomethyl ketone. This base was converted to the methanesulfonate by treatment, in 200 ml. of warm N,N-dimethylformamide, with methanesulfonic acid. The 3-hydroxy-4-(p-toluyloxy)phenyl tert-butylaminomethyl ketone methanesulfonate thus obtained was a white crystalline solid which weighed 12 g. and melted at 265° C. (dec.)(uncorr.).

Sources & evidence

ORD record
ord-58ae942cccc4450a970952def72c33a8
Source dataset
uspto-grants-1982_06
Patent number
US04336400

Reaction notes

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