1-(p-Chlorophenyl)acetone → Ethyl 2-(7-chloro-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

HRID 514150Notes

Reaction equation

HRID 514150 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[C:8]([OH:13])=[C:7]([CH:14]([OH:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]([CH3:21])=[CH:5]2.[Cl:22]C1C=CC(CC(=O)C)=CC=1>>[Cl:22][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([CH3:21])[C:7]([CH:14]([OH:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:8]2[OH:13])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 796991-(p-Chlorophenyl)acetoneHCID 67126131Ethyl 2-(6-chloro-7-fluoro-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 67126269Ethyl 2-(7-chloro-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Procedure

Prepared in a manner similar to ethyl 2-(6-chloro-7-fluoro-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate of Example 99 except using 1-(4-chlorophenyl)propan-2-one. 1H-NMR: (400 MHz, CDCl3): δ 8.42 (s, broad, 1H), 8.18 (d, J=2.0 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.38 (dd, J=8.6, 2.0 Hz, 1H), 7.18 (s, 1H), 5.68 (s, 1H), 4.33-4.10 (m, 2H), 2.53 (s, 3H), 1.20 (t, J=7.0 Hz, 3H).

Sources & evidence

ORD record
ord-015fb397072b4cc38ab1a6af836b448e
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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