Phenolate Sodium → HCID 54364113, compound

HRID 1156679Notes

Reaction equation

[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:11]([OH:27])[CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C1([O-])C=CC=CC=1.[Na+].[CH:39]([O:42][C:43]1[CH:48]=[CH:47][C:46]([CH2:49][C:50](Cl)=[O:51])=[CH:45][CH:44]=1)([CH3:41])[CH3:40]>>[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:11]([O:27][C:50](=[O:51])[CH2:49][C:46]2[CH:47]=[CH:48][C:43]([O:42][CH:39]([CH3:40])[CH3:41])=[CH:44][CH:45]=2)[CH:10]=1)=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 4445035Phenolate Sodium

HCID 10942334Sodium Methoxide

HCID 14696615HCID 14696615, compound

HCID 20535365HCID 20535365, compound

Product 1

HCID 54364113HCID 54364113, compound

Procedure

Following a procedure similar to that described in Example 30A above, when 3-hydroxy-4-(7,7-dimethyloctanoyloxy)-phenyl tert-butylaminomethyl ketone is interacted with one equivalent of sodium methoxide and the resulting sodium phenolate salt is reacted with p-isopropoxyphenylacetyl chloride there is obtained 3-(p-isopropoxyphenylacetoxy)-4-(7,7-dimethyloctanoyloxy)phenyl tert-butylaminomethyl ketone which reacts with methanesulfonic acid to yield the methanesulfonate salt. When this methanesulfonate is catalytically hydrogenated, using the procedure described above in Example 30B, there is obtained 3-(p-isopropoxyphenylacetoxy)-4-(7,7-dimethyloctanoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol methanesulfonate.

Sources & evidence

ORD record: ord-c9ddcbdba78b4955892a121b1b2a7ab9
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04336400

Reaction notes

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