Formaldehyde → HCID 57095110, compound

HRID 1457955Notes

Reaction equation

[CH2:1]([NH:8][CH:9]1[CH:15]([OH:16])[C:14]([CH3:18])([CH3:17])[CH2:13][C:12](=[O:19])[C:11]([CH3:20])=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]=O>C(O)=O>[OH:16][CH:15]1[C:14]([CH3:17])([CH3:18])[CH2:13][C:12](=[O:19])[C:11]([CH3:20])=[CH:10][CH:9]1[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

The 4-benzylamino-5-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one obtained in Example 1 (5.86 g, 21.5 millimoles) was dissolved in formic acid (30 ml), formalin (30 ml) was added, and the mixture was heated at 90° C. for 3 hours. The reaction solution was concentrated and alkalified with a 1% aqueous sodium hydroxide solution. The aqueous solution was subjected to extraction with benzene, washed with water, and then dried over anhydrous potassium carbonate. The benzene solution was concentrated, and the resulting residue was subjected to silica gel column chromatography with hexane-ethyl acetate (9:1) as the eluent, to obtain 2.95 g of crude product which was then recrystallized from hexane to give 2.39 g (39%) of 5-hydroxy-4-(N-methylbenzylamino)-2,6,6-trimethyl-2-cyclohepten-1-one as colorless crystals. Melting point: 78.5°~80° C.

Workup

concentrationThe reaction solution was concentrated
extractionThe aqueous solution was subjected to extraction with benzene
washwashed with water
dry with materialdried over anhydrous potassium carbonate
concentrationThe benzene solution was concentrated
customto obtain 2.95 g of crude product which
customwas then recrystallized from hexane

Sources & evidence

ORD record: ord-4d53cb26cad34bd0a22d6e76115c423e
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849801

Reaction notes

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