Hydrochloric Acid → HCID 12295087, compound

HRID 1701657Notes

Reaction equation

HRID 1701657 reaction equation
Cl.C(NCC(C(C1C=CC(O)=C(O)C=1)=O)C)(C)(C)C.C([Cl:26])(=O)C(C)(C)C.FC(F)(F)C(O)=O.Cl.Cl.[C:36]([NH:40][CH2:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])=[C:46]([O:57][C:58](=[O:63])[C:59]([CH3:62])([CH3:61])[CH3:60])[CH:45]=1)=[O:43])([CH3:39])([CH3:38])[CH3:37]>[Pd]>[ClH:26].[C:58]([O:57][C:46]1[CH:45]=[C:44]([CH:49]=[CH:48][C:47]=1[O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[CH:42]([OH:43])[CH2:41][NH:40][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:63])[C:59]([CH3:62])([CH3:60])[CH3:61]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 62493Pivaloyl chlorideHCID 12295037HCID 12295037, compoundHCID 20345977HCID 20345977, compound

Product 1

HCID 12295087HCID 12295087, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3,4-Dihydroxyphenyl 1-(tert-butylaminomethyl)ethyl ketone hydrochloride (8 g.) was reacted with 18 ml. of pivalyl chloride in 35 ml. of trifluoroacetic acid, the resulting ester-amine salt was converted to the ester-amine, and the ester-amine was treated with hydrochloric acid to yield 10.5 g. of 3,4-bis-(pivalyloxy)phenyl tert-butylaminomethyl ketone hydrochloride, m.p. 200°-202° C. (uncorr.). This ketone was catalytically hydrogenated in the presence of palladium-on-charcoal catalyst to yield 3,4-bis(pivalyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride as a white crystalline solid which melted at 205°-207° C. (uncorr.).

Workup

  1. customto yield 10.5 g

Sources & evidence

ORD record
ord-40313f5be58341e482bce4095706cba7
Source dataset
uspto-grants-1980_03
Patent number
USRE030241

Reaction notes

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