Acetic Acid → Methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoate

HRID 2371796Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)#N.O.[PH2]([O-])=[O:28].[Na+].C(O)(=O)C.N1C=CC=CC=1>[Ni].O>[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)=[O:28]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate (1.06 g), sodium hypophosphite hydrate (2.25 g), glacial acetic acid (4 ml), pyridine (8 ml) and water (4 ml) was added Raney nickel (330 mg of material resulting from decanting water from a 50% (w/w) slurry in water). The reaction mixture was heated to 50° C. for 1 h and cooled, ethyl acetate was added and the mixture filtered through diatomaceous earth with ethyl acetate wash. The organic layer was washed (1N HCl twice, brine), dried (MgSO4) and evaporated. Purification by flash chromatography, eluting with methylene chloride, and trituration with ether afforded methyl 4-(7-formylnaphth-1-ylmeth-yl)-3-methoxybenzoate (506 mg, 47%) as a colorless solid; mp 103°-4° C., MS(CI), m/e=336(M+H).

Workup

customresulting
customfrom decanting water from a 50% (w/w) slurry in water)
temperaturecooled
additionethyl acetate was added
filtrationthe mixture filtered through diatomaceous earth with ethyl acetate
washwash
washThe organic layer was washed (1N HCl twice
dry with materialbrine), dried (MgSO4)
customevaporated
customPurification by flash chromatography
washeluting with methylene chloride, and trituration with ether

Sources & evidence

ORD record: ord-7d45dc63a04046f8a8925eb07ec74fbd
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05095038

Reaction notes

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