Ammonium Chloride → alpha-Methyl-4-(trifluoromethoxy)benzenemethanol
Reaction equation
[CH3:1][Mg]I.[F:4][C:5]([F:16])([F:15])[O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[Cl-].[NH4+]>C(OCC)C.O>[F:4][C:5]([F:15])([F:16])[O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]([OH:12])[CH3:1])=[CH:9][CH:8]=1Participants
Procedure
Methyl magnesium iodide [prepared from magnesium (3.5 g) and methyl iodide (20.5 g)] in diethyl ether (50 ml) was treated with a solution of 4-trifluoromethoxybenzaldehyde [20 g, described by Yagupolskii and Troitskaya, Zhur. Obschii Khim., 30, 3129 (1960)] in diethyl ether (25 ml) at reflux with stirring. After the addition the mixture was heated at reflux for 6 hours. The cooled solution was treated with a solution of ammonium chloride (35 g) in water (100 ml) at 0°-5° C. The organic layer was separated and the aqueous layer was washed with diethyl ether (3×50 ml). The ether solution and washings were combined, washed with water (2×100 ml), dried over sodium sulphate and evaporated to dryness. (+)-1-(4-Trifluoromethoxyphenyl)ethanol (20.3 g) was obtained as a clear colourless oil of sufficient purity for subsequent reaction.
Workup
- temperatureat reflux
- additionAfter the addition the mixture
- temperaturewas heated
- temperatureat reflux for 6 hours
- customThe organic layer was separated
- washthe aqueous layer was washed with diethyl ether (3×50 ml)
- washwashed with water (2×100 ml)
- dry with materialdried over sodium sulphate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1407e2408e794068ba48d40ad1efbfb1
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04185992
Reaction notes
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