Benzoyl chloride → Ethyl 8-(1-naphthyl)-8-oxooctanoate

HRID 1182462Notes

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>>[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])[C:7]2[C:6](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 10934282Ethyl 8-oxo-8-phenyloctanoate

Product 1

HCID 23072485Ethyl 8-(1-naphthyl)-8-oxooctanoateYield 58%

Procedure

Following a procedure analogous to that described above for 49a, but substituting 1-naphthoyl chloride for benzoyl chloride, the title compound was obtained as a white solid in 58% yield: 1H NMR (300 MHz, CDCl3) δ 8.56 (d, J=8.7 Hz, 1H), 7.42-7.92 (m, 6H), 4.10 (q, J=6.9 Hz, 2H), 2.98 (m, 2H), 2.26(t, J=7.5 Hz, 2H), 1.75 (m, 2H), 1.62 (m, 2H), 1.36 (m, 4H), 1.22 (t, J=6.9 Hz, 3H); 13C NMR (75.4 MHz, CDCl3) δ 14.02, 24.23, 24.55, 28.70(2), 33.98, 41.79, 59.89, 124.12, 125.51, 126.12, 126.99, 127.51, 128.14, 129.87, 132.06, 133.69, 136.00, 173.39, 204.44.

Sources & evidence

ORD record: ord-bd1e4f68d6264483964b692fa7cc8314
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288567B2

Reaction notes

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