1-Chloromethylnaphthalene → 2-(Naphthalen-1-ylmethoxy)benzaldehyde

HRID 1795113

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[C:12]1([CH2:11][O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-hydroxybenzaldehyde (2.30 g, 18.8 mmol) in DMF (20 mL) is added 1-(chloromethyl)-naphthalene (3.36 mL, 22.6 mmol) and K2CO3 (3.11 g, 22.6 mmol), and the reaction mixture is heated to 100° C. for 12 h. Once complete, the reaction mixture is cooled to room temperature and diluted with water (100 mL) prior to being poured into a separatory funnel containing ethyl acetate (250 mL). The organic layer is separated, washed with brine (2×) and dried over sodium sulfate prior to concentration. The crude product is purified by column chromatography (5% ethyl acetate in hexanes) to afford 2-(1-naphthylmethoxy)benzaldehyde (2.13 g, 43%) as a light yellow oil.

Workup

temperatureOnce complete, the reaction mixture is cooled to room temperature
additionto being poured into a separatory funnel
customThe organic layer is separated
washwashed with brine (2×)
dry with materialdried over sodium sulfate
concentrationto concentration
customThe crude product is purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-3f39b2fc764a4dc582d690e962a26da4
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026339B2

Linked notes

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