Sodium Hydroxide → HCID 18401029, compound

HRID 1019361Notes

Reaction equation

HRID 1019361 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:15]([OH:21])([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:7]([CH2:9][CH2:10][O:11]C(=O)C)[CH:8]=1.[OH-].[Na+]>O>[F:17][C:16]([F:18])([F:19])[C:15]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH2:9][CH2:10][OH:11])([OH:21])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59921413HCID 59921413, compound

Product 1

HCID 18401029HCID 18401029, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the crude reaction mixture described in example 3 containing acetic acid 2-[5-methoxy-2-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl ester was added 1N aqueous sodium hydroxide (75.0 mL, 75 mmol). The reaction mixture was allowed to warm to room temperature and was stirred 12 hours. The reaction mixture was poured into water (75 mL) and extracted with methyl tert-butyl ether (150 mL). The organic layer was washed with water (75 mL) and brine (75 mL), dried over magnesium sulfate, and concentrated to an oil. To the crude oil was added hexanes (20 mL) and methyl tert-butyl ether (4 mL) and a solid precipitated. The mixture was stirred for 30 minutes and filtered to provide 1,1,1-trifluoro-2-[2-(2-hydroxy-ethyl)-4-methoxy-phenyl]-propan-2-ol (7.3 g, 52% overall yield from acetic acid 2-(2-acetyl-5-methoxy-phenyl)-ethyl ester). M.p. 110-111° C. 1H NMR (300 MHz, CDCl3) δ1.83 (s, 3), 2.91 (dt, 1, J=13.7, 3.9), 3.76 (ddd, 1, J=13.7, 9.3, 4.4), 3.85 (s, 3), 3.85-3.93 (m, 1), 4.08 (dt, 1, J 9.3, 3.7), 6.80-6.83 (m, 2), 7.38 (d, 1, J=8.4). 13C NMR (100 MHz, CDCl3) δ26.01, 36.12, 55.19, 64.13, 76.52 (q, J=28.9), 111.47, 117.43, 125.99 (q, J=287), 129.69, 129.94, 140.86, 159.55. IR 3395, 3162, 1610, 1513, 1467, 1248, 1157, 1087, 1046 cm−1. Analysis calculated for C12H15F3O3: C, 54.54; H, 5.72. Found: C, 54.65; H, 5.70.

Workup

  1. customTo the crude reaction mixture
  2. extractionextracted with methyl tert-butyl ether (150 mL)
  3. washThe organic layer was washed with water (75 mL) and brine (75 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to an oil
  6. additionTo the crude oil was added hexanes (20 mL) and methyl tert-butyl ether (4 mL)
  7. customa solid precipitated
  8. stirringThe mixture was stirred for 30 minutes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-85304c20811f485f9fd0b330201722ec
Source dataset
uspto-grants-2002_11
Patent number
US06486325B1

Reaction notes

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