Diethyl Ether → 2-Ethyl-4-(hydroxymethyl)phenol
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[OH:11])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-ethyl-4-hydroxybenzaldehyde (4.7 g, 26 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added dropwise 1 M LiAlH4 in Et2O (52 mL, 52.2 mmol). The resulting mixture was stirred at 0° C. for 2 h and then quenched by cautious addition of water and stirred for 15 minutes. The reaction mixture was then absorbed onto silica and loaded onto a silica pad which was washed with EtOAc. The EtOAc washings were collected and concentrated in vacuo to afford the title compound as a colourless oil (3.67 g).
Workup
- customquenched by cautious addition of water
- stirringstirred for 15 minutes
- customThe reaction mixture was then absorbed onto silica
- washwas washed with EtOAc
- customThe EtOAc washings were collected
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8c2e015437b54ae2bf465a8aefff7d9c
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199239B2
Reaction notes
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