Ethanol → 4-(2-Hydroxybenzylideneamino)-1-naphthol

HRID 434720Notes

Reaction equation

[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C([O-])(=O)C.[Na+].C(O)C.Cl.[NH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([OH:30])=[CH:22][CH:21]=1>O>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[N:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([OH:30])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer and drying tube was added 5.50 grams (0.045 moles) of salicylaldehyde, 4.10 grams (0.050 moles) of sodium acetate and 40 milliliters of ethanol. The resulting mixture was then heated to a temperature of 50° C. and a solution consisting of 7.83 grams (0.040 moles) of 4-amino-1-naphthol hydrochloride in 20 milliliters of water was added thereto. The resulting reaction mixture was stirred for 15 minutes at a temperature of 50° C. and then cooled to room temperature forming a precipitate. The precipitate was removed from the reaction mixture by filtration, washed with water and dried over magnesium sulfate to give 8.68 grams (0.033 moles) of 4-(2-hydroxybenzylideneamino)-1-naphthol in the form of reddish-brown crystals having a melting point of 153.5°-157° C.

Workup

customTo a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer
customdrying tube
additionwas added
customThe resulting reaction mixture
temperaturecooled to room temperature
customforming a precipitate
customThe precipitate was removed from the reaction mixture by filtration
washwashed with water
dry with materialdried over magnesium sulfate

Sources & evidence

ORD record: ord-1b044ad61c654d5a9d05b7a0be61ef3f
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04399148

Reaction notes

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