Hydrochloric Acid → Acetyl chloride

HRID 1701653Notes

Reaction equation

HRID 1701653 reaction equation
[ClH:1].C(N[CH2:7][C:8](C1C=CC(O)=C(O)C=1)=[O:9])(C)(C)C.C[O-].[Na+].[C:21]([Cl:31])(=[O:30])[C:22]1C=CC(OC)=CC=1.[C:32]([NH:36][CH2:37][C:38]([C:40]1[CH:45]=[CH:44][C:43]([O:46][C:47](=[O:56])[C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)=[C:42]([OH:57])[CH:41]=1)=[O:39])([CH3:35])([CH3:34])[CH3:33].Cl.Cl.[OH:60][C:61]1[CH:62]=[C:63]([CH:72]=[CH:73][C:74]=1[O:75][C:76](=[O:85])[C:77]1[CH:82]=[CH:81][C:80]([O:83][CH3:84])=[CH:79][CH:78]=1)[CH:64]([OH:71])[CH2:65][NH:66][C:67]([CH3:70])([CH3:69])[CH3:68]>CN(C)C=O>[C:21]([Cl:31])(=[O:30])[CH3:22].[ClH:1].[C:64]([O:39][CH:38]([CH2:37][NH:36][C:32]([CH3:35])([CH3:33])[CH3:34])[C:40]1[CH:45]=[CH:44][C:43]([O:46][C:47](=[O:56])[C:48]2[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=2)=[C:42]([OH:57])[CH:41]=1)(=[O:71])[C:63]1[CH:72]=[CH:73][C:74]([O:75][CH3:76])=[CH:61][CH:62]=1.[ClH:31].[C:8]([O:71][CH:64]([CH2:65][NH:66][C:67]([CH3:70])([CH3:69])[CH3:68])[C:63]1[CH:72]=[CH:73][C:74]([O:75][C:76](=[O:85])[C:77]2[CH:78]=[CH:79][C:80]([O:83][CH3:84])=[CH:81][CH:82]=2)=[C:61]([OH:60])[CH:62]=1)(=[O:9])[CH3:7]

Participants

10

Reactant 6

HCID 313Hydrochloric Acid3×HCID 7477p-Anisoyl chloride2×HCID 30157041-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochlorideHCID 10942334Sodium MethoxideHCID 122950263-Hydroxy-4-(p-anisoyloxy)phenyl tert-butylaminomethyl ketoneHCID 122950773-Hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride

Product 3

HCID 6367Acetyl chlorideHCID 20535421HCID 20535421, compoundHCID 86736300HCID 86736300, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a procedure similar to that described above in Example 58A, 26 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride was reacted with 16 g. of sodium methoxide in N,N-dimethylformamide under an atmosphere of nitrogen and then 17 g. of p-anisoyl chloride was added to produce 35 g. of 3-hydroxy-4-(p-anisoyloxy)phenyl tert-butylaminomethyl ketone, m.p. 170°-175° C. (dec.)(uncorr.), which was converted to 28 g. of the hydrochloride, m.p. 235° C. (dec.)(uncorr.). This hydrochloride (26 g.) was catalytically hydrogeated, using a procedure similar to that described above in Example 30B, to yield 19 g. of 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride as a white crystalline solid which melted at 211°-213° C. (dec.)(uncorr.). By interacting this hydrochloride with p-anisoyl chloride and with acetyl chloride, there are obtained 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl p-anisate hydrochloride and 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl acetate hydrochloride, respectively.

Workup

  1. customto produce 35 g
  2. customto yield 19 g

Sources & evidence

ORD record
ord-143aee4f754744be90da5d2ee21fb224
Source dataset
uspto-grants-1980_03
Patent number
USRE030241

Reaction notes

Loading…