2-Trifluoromethylphenol → 1-[(1R)-3-Chloro-1-phenylpropoxy]-4-(trifluoromethyl)benzene

HRID 1608085Notes

Reaction equation

HRID 1608085 reaction equation
[Cl:1][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[F:12][C:13]([F:22])([F:21])[C:14]1[C:19](O)=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[Cl:1][CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[O:5][C:17]1[CH:18]=[CH:19][C:14]([C:13]([F:22])([F:21])[F:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 679582-TrifluoromethylphenolHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

Product 1

HCID 111744911-[(1R)-3-Chloro-1-phenylpropoxy]-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the method of example 55 using [S]-3-chloro-1-phenylpropanol (2.57g, 15 mmol), α,α,α-trifluoro-cresol (2.4 g, 15 mmol) in THF (40 ml) at room temperature. Workup provided the optically pure title compound as a thick liquid, bp 180°-200° C./0/5 mm. [α]D +2.3° (c 10, CHCl3 ; 13C NMR (CDCl3): 140.50, 129.39, 128.66, 127,56, 127.38, 127.19, 127.01, 126.34, 116.45, 77.82, 41.69, 41.38. Mass spectrum (EI): 153/155 (45), 91 (100). (CI): 314/316, (1, M+), 153/155 (100). Anal. Calcd. for C16H14ClNO: C, 61.05; H, 4.45; Cl, 11.29; F, 18.12. Found: C, 61.06; H, 4.51; Cl, 11.16; F, 18.22.

Sources & evidence

ORD record
ord-d175e6a4fa384a06ad6ef1fe88d9bc17
Source dataset
uspto-grants-1989_09
Patent number
US04868344

Reaction notes

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