Hydrochloric Acid → 9-(2',3',4'-Trimethoxy-6'-methylbenzoyl)nonanoic acid

HRID 647036Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:7].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH3:33])[CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30].Cl>[N+](C1C=CC=CC=1)([O-])=O>[CH3:32][O:31][C:27]1[C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=[C:25]([CH3:33])[C:26]=1[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Under cooling with ice, aluminum chloride (4.08 parts) was added in small portions to a mixed solution of ethyl 9-chloroformylnonanoate (3.52 parts) and 3,4,5-trimethoxytoluene (formula VII wherein R=H3CO, X=H, Y=H3CO) (2.21 parts) in nitrobenzene (20 volume parts). The mixture was stirred at 0° C. for 16 hours and, then, at room temperature for 1.5 hours. The reaction mixture was rendered acidic with dilute hydrochloric acid and extracted with diethyl ether. By a procedure similar to that described in Example 1 (2), the extract was hydrolyzed and subjected to column chromatography on silicic acid. The fraction eluted by benzenediethyl ether (9:1) yielded 9-(2',3',4'-trimethoxy-6'-methylbenzoyl)nonanoic acid (formula II-1 wherein R=H3CO, X=H, Y=OCH3, n=8, in the free form) (1.82 part). From the fraction eluted by benzene-diethyl ether (5.7:1), there was obtained 9-(2'-hydroxy-3',4'-dimethoxy-6' -methylbenzoyl)nonanoic acid (formula II-1, R=H3CO, X=H, Y=OH, n=8 in the free form) (0.67 part) as colorless needles melting at 75°-76.5° C.

Workup

waitat room temperature for 1.5 hours
extractionextracted with diethyl ether
washThe fraction eluted by benzenediethyl ether (9:1)

Sources & evidence

ORD record: ord-0426c6d2dbdb4a8eadef87fb12c666f8
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04407757

Reaction notes

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