Benzenemethanol, 2,6-bis(trifluoromethyl)- synthesis
- Product Name:Benzenemethanol, 2,6-bis(trifluoromethyl)-
- CAS Number:152211-16-0
- Molecular formula:C9H6F6O
- Molecular Weight:244.1338
Yield:152211-16-0 40%
Reaction Conditions:
Stage #1: 1,3-bis(trifluoromethyl)benzenewith potassium tert-butylate in tetrahydrofuran at -70; for 0.5 h;
Stage #2: with n-butyllithium in tetrahydrofuran;hexane at -70; for 1.5 h;
Stage #3: formaldehyd in tetrahydrofuran;hexane at -70 - 20; for 3.5 h;
Steps:
23 (2,6-bis(trifluoromethyl)phenyl)methanol (JM3-1352-2)
To a solution of KOtBt (1.3 g, 11.62 mmol) in THF at -70° C. was added 2,6-bis(trifluoromethyl)benzene (2.0 g, 9.3 mmol) dropwise over a period of 30 min.
To this solution was added n-BuLi (18.6 mmol, 2.5 M in hexanes) dropwise for 30 min, stirring continued at -70° C. for 60 min.
To this mixture was added Paraformaldehyde (61.2 g, 37.2 mmol) and stirring continued at -70° C. for 30 min, then allowed to room temperature for 3 h.
The reaction mixture was poured into conc. HCl (2 mL) and ice water (60 mL) and stirred for 1 h, extracted with hexanes (3*10 mL) and washed with brine, dried over Na2SO4, and concentrated in vacuo to get final compound as dark brown oil (40%). ESI-MS (M)+ 244.03.
References:
US2018/230105,2018,A1 Location in patent:Paragraph 0396; 0397
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