1-(2-Methoxynaphthalen-1-yl)-2-oxopropyl acetate → 1-Hydroxy-1-(2-methoxy-naphthalen-1-yl)-propan-2-one

HRID 33574Notes

Reaction equation

HRID 33574 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]([O:17]C(=O)C)[C:14](=[O:16])[CH3:15].[CH3:21][O:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]=1[C:33](=[O:40])[CH:34]([O:36]C(=O)C)[CH3:35]>>[OH:16][CH:14]([CH3:15])[C:13]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])=[O:17].[OH:40][CH:33]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[O:22][CH3:21])[C:34](=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 141135501-(2-Methoxynaphthalen-1-yl)-2-oxopropyl acetateHCID 59796867Acetic acid 2-(2-methoxy-naphthalen-1-yl)-1-methyl-2-oxo-ethyl ester

Product 2

HCID 59796849HCID 59796849, compoundHCID 597968701-Hydroxy-1-(2-methoxy-naphthalen-1-yl)-propan-2-oneYield 59%

Procedure

2-hydroxy-1-(2-methoxy-naphthalen-1-yl)-propan-1-one and 1-hydroxy-1-(2-methoxy-naphthalen-1-yl)-propan-2-one (4.5:1 mixture) (580 mg, 59%) were prepared from acetic acid 1-(2-methoxy-naphthalen-1-yl)-2-oxo-propyl ester and acetic acid 2-(2-methoxy-naphthalen-1-yl)-1-methyl-2-oxo-ethyl ester (3:1 mixture) according to the method in Example 16A(c) as an orange solid, 1H NMR (CDCl3): 1.3 (3H, d, J=7.2 Hz), 2.0 (3H, s), 3.75 (1H, d, J=5.0 Hz), 3.9 (3H, s), 3.95 (3H, s), 4.2 (1H, d, J=3.5 Hz), 5.0 (1H, m), 5.9 (1H, d, J=3.5 Hz), 7.25-7.30 (2H, m), 7.35-7.40 (2H, m), 7.45-7.50 (2H, m), 7.6 (1H, d, J=7.7 Hz), 7.75 (2H, m), 7.85 (1H, d, J=9.0 Hz), 7.90-7.95 (2H, m).

Sources & evidence

ORD record
ord-8c2444aeac334f92a1ac0bd9ad41b3a6
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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