3-Methyl-1,2,3,4-tetrahydronaphthalen-1-one → Ethyl 2-(4-methoxybenzyloxy)-2-(1-hydroxy-3-methylnaphthalen-2-yl)acetate

HRID 514119Notes

Reaction equation

HRID 514119 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([C:16]1[C:25]([CH3:26])=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2OC)[C:17]=1[OH:29])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:2].CC1CC2C(=CC=CC=2)C(=O)C1>>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][O:6][CH:5]([C:16]2[C:25]([CH3:26])=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[OH:29])[C:4]([O:3][CH2:1][CH3:2])=[O:30])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 857903-Methyl-1,2,3,4-tetrahydronaphthalen-1-oneHCID 67126070(1-Hydroxy-5-methoxy-3-methyl-naphthalen-2-yl)-(4-methoxy-benzyloxy)-acetic acid ethyl ester

Product 1

HCID 67126181Ethyl 2-(4-methoxybenzyloxy)-2-(1-hydroxy-3-methylnaphthalen-2-yl)acetate

Procedure

Ethyl 2-(4-methoxybenzyloxy)-2-(1-hydroxy-3-methylnaphthalen-2-yl)acetate was prepared in a similar manner as (1-hydroxy-5-methoxy-3-methyl-naphthalen-2-yl)-(4-methoxy-benzyloxy)-acetic acid ethyl ester of Example 32, except using 3-methyl-3,4-dihydronaphthalen-1(2H)-one. 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.48-7.36 (m, 2H), 7.27 (d, 8.5 Hz, 2H), 7.18 (s, 1H), 6.89 (d, J=8.4 Hz, 2H), 5.30 (s, 1H), 4.67-4.55 (m, 2H), 4.27-4.08 (m, 2H), 3.82 (s, 3H), 2.40 (s, 3H), 1.19 (t, J=7.0 Hz, 3H).

Sources & evidence

ORD record
ord-dcd4cc44c21347cda9aae66a43572328
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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