Sodium Hydroxide → 3-Methoxy-4-(trifluoromethyl)benzyl alcohol

HRID 1375001Notes

Reaction equation

HRID 1375001 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19])[C:12](O)=[O:13].[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]([F:19])([F:20])[F:21])[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 179641303-Methoxy-4-(trifluoromethyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 539937923-Methoxy-4-(trifluoromethyl)benzyl alcoholYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (4.53 g) was added by small portions to an ice-cooled solution of 3-methoxy-4-(trifluoromethyl)benzoic acid (23.3 g) in tetrahydrofuran (400 ml) under nitrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. After being cooled with ice, 2N sodium hydroxide (2 ml) was added to the mixture under nitrogen atmosphere. The resulting precipitates were filtered off and washed with tetrahydrofuran, and the filtrate and washings were combined and evaporated under reduced pressure to give a crude oil. The oil was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (40:1) to give 3-methoxy-4-(trifluoromethyl)benzyl alcohol (20 g) as a colorless oil.

Workup

  1. additionwas added to the mixture under nitrogen atmosphere
  2. customThe resulting precipitates
  3. filtrationwere filtered off
  4. washwashed with tetrahydrofuran
  5. customevaporated under reduced pressure
  6. customto give a crude oil
  7. customThe oil was purified by column chromatography on silica gel using
  8. additiona mixture of dichloromethane and methanol (40:1)

Sources & evidence

ORD record
ord-f272355c0b4c4143b043de4f47427194
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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