Dimethylformamide → 3,4-Bis(pivalyloxy)phenyl tert-butylaminomethyl ketone

HRID 1390433Notes

Reaction equation

HRID 1390433 reaction equation
[CH3:1][O-].[Na+].Cl.[C:5]([NH:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([OH:20])[CH:14]=1)=[O:12])([CH3:8])([CH3:7])[CH3:6].[C:21]1([O-])[CH:26]=[CH:25]C=CC=1.[Na+].[C:29](Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].CN(C)[CH:38]=[O:39]>>[C:5]([NH:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:15]([O:20][C:38](=[O:39])[C:26]([CH3:25])([CH3:21])[CH3:1])[CH:14]=1)=[O:12])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 62493Pivaloyl chloride3×HCID 30157041-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochlorideHCID 4445035Phenolate SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 122950363,4-Bis(pivalyloxy)phenyl tert-butylaminomethyl ketone

Procedure

Proceeding in a manner similar to that described in part A of Example 2 above, 17 g. of sodium methoxide was interacted with 26 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride in 200 ml. of N,N-dimethylformamide and the resulting sodium phenolate salt was interacted with 24 g. of pivalyl chloride (alternatively designated as trimethylacetyl chloride or 2,2-dimethylpropanoyl chloride). From this acylation reaction there was obtained 3,4-bis(pivalyloxy)phenyl tert-butylaminomethyl ketone which was treated with hydrochloric acid to yield 11.5 g. of 3,4-bis(pivalyloxy)phenyl tert-butylaminomethyl ketone hydrochloride as a white crystalline solid which melted at 243- 244° C. (dec.)(uncorr.). This salt was soluble in water at 25° C. to the extent of at least 1 per cent.

Workup

  1. customFrom this acylation reaction

Sources & evidence

ORD record
ord-391da45e269845ac857c558e871896fd
Source dataset
uspto-grants-1979_02
Patent number
US04138581

Reaction notes

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