4-Chlorotoluene → HCID 54241161, compound

HRID 1390473Notes

Reaction equation

[CH:1]([NH:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18])=[C:10]([OH:21])[CH:9]=1)=[O:7])([CH3:3])[CH3:2].C[O-].[Na+].C1([O-])C=CC=CC=1.[Na+].[C:33]1([CH3:40])[CH:38]=[CH:37][C:36](Cl)=[CH:35][CH:34]=1>>[CH:1]([NH:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18])=[C:10]([O:21][C:36]2[CH:37]=[CH:38][C:33]([CH3:40])=[CH:34][CH:35]=2)[CH:9]=1)=[O:7])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 78104-Chlorotoluene

HCID 4445035Phenolate Sodium

HCID 10942334Sodium Methoxide

HCID 20535287HCID 20535287, compound

Product 1

HCID 54241161HCID 54241161, compound

Procedure

Following a procedure similar to that described above in Example 2A, when 3-hydroxy-4-(isovaleryloxy)phenyl isopropylaminomethyl ketone is interacted with one equivalent of sodium methoxide and the resulting sodium phenolate salt is reacted wirh p-toluyl chloride there is obtained 3-(p-toluyloxy)-4-(isovaleryloxy)phenyl isopropylaminomethyl ketone; and by interaction of this base with hydrochloric acid there is obtained the hydrochloride salt. When this hydrochloride is catalytically hydrogenated, using a procedure similar to that described above in Example 2B, there is obtained 3-(p-toluyloxy)-4-(isovaleryloxy)-alpha-(isopropylaminomethyl)benzyl alcohol hydrochloride.

Sources & evidence

ORD record: ord-33cd9972d90e45588199522962b3d814
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04138581

Reaction notes

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