Benzoyl chloride → ETHYL 8-(2-NAPHTHYL)-8-OXOOCTANOATE

HRID 1182463Notes

Reaction equation

[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=O)[C:21]1C=CC=[CH:23][CH:22]=1>>[CH:3]1[C:4]2[C:5](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:6]=[CH:7][C:2]=1[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:8]

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 10934282Ethyl 8-oxo-8-phenyloctanoate

Product 1

HCID 10881518ETHYL 8-(2-NAPHTHYL)-8-OXOOCTANOATEYield 54%

Procedure

Following a procedure analogous to that described above for 49a, but substituting 2-naphthoyl chloride for benzoyl chloride, the title compound was obtained as a white solid in 54% yield: 1H NMR (300 MHz, CDCl3): δ 8.47 (s, 1H), 7.86-8.05 (m, 4H), 7.51-7.62 (m, 2H), 4.12 (q, J=6.9 Hz, 2H), 3.10 (t, J=7.5 Hz, 2H), 2.31 (t, J=7.5 Hz, 2H), 1.80 (m, 2H), 1.62 (m, 2H), 1.41 (m, 4H), 1.25 (t, J=6.9 Hz, 3H).

Sources & evidence

ORD record: ord-311b83b3822d48c3bf43d091080a069b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288567B2

Reaction notes

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