Ethanol → 1-(3-Methoxyphenyl)propan-2-ol

HRID 1992974Notes

Reaction equation

HRID 1992974 reaction equation
C([O:3][C:4](=[O:36])[C:5](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=3)[CH:20]=[C:19]([CH3:29])[C:18]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:12][CH:11]=1)[CH:6]([CH3:8])[CH3:7])C.[OH-].[Na+].CCO>C1COCC1>[CH3:13][O:16][C:17]1[CH:26]=[C:21]([CH2:22][CH:23]([OH:27])[CH3:24])[CH:20]=[CH:19][CH:18]=1.[CH3:28][O:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[C:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([CH:9]=[C:5]([CH:6]([CH3:8])[CH3:7])[C:4]([OH:36])=[O:3])=[CH:15][CH:14]=1)=[C:18]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:19]([CH3:29])=[CH:20]2

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 685360972-[4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzylidene]-3-methyl-butyric acid ethyl ester

Product 2

HCID 124998521-(3-Methoxyphenyl)propan-2-olYield 505.3%HCID 685363952-[4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzylidene]-3-methyl-butyric acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 31 (Step 4), isomer (1) of 2-[4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzylidene]-3-methyl-butyric acid ethyl ester (222-1) (0.159 g, 0.331 mmol), 1 N NaOH (4 mL), EtOH (3 mL) and THF (3 mL) afforded isomer (1) (223-1) 0.139 g (93%) of the title compound. 1H NMR (400 MHz, d-CDCl3): δ 1.22 (d, J=7.0 Hz, 6H), 2.23 (s, 3H), 3.08-3.15 (m, 1H), 3.93 (s, 3H), 6.58 (d, J=8.6 Hz, 2H), 7.04-7.07 (m, 3H), 7.12-7.13 (m, 3H), 7.20-7.28 (m, 4H), 7.54 (d, J=13.4, 2H), 7.76 (d, J=9.1 Hz, 1H).

Sources & evidence

ORD record
ord-032c0e6cb0634b82aed3595e0fa59b0b
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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