Water → 4-(Trifluoromethoxy)benzenemethanol

HRID 1084788Notes

Reaction equation

HRID 1084788 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:19])([F:18])[O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#N)=[CH:12][CH:11]=1.[OH2:20].[OH-].[Na+]>C(OCC)C>[F:7][C:8]([F:19])([F:18])[O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:20])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 676214-(Trifluoromethoxy)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 1371844-(Trifluoromethoxy)benzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of lithium aluminium hydride in diethyl ether (1.0M, 69.4 ml) was added dropwise to a stirred solution of 4-(trifluoromethoxy)benzonitrile (6.0 g) in diethyl ether (120 ml) over 15 minutes. Water (2.66 ml), 10% sodium hydroxide solution (2.66 ml) and water (7.98 ml) were then added successively, dropwise. The precipitated solid was filtered off and washed with diethyl ether. The filtrate and washings were combined and evaporated under reduced pressure to give 4-(trifluoromethoxy)benzyl alcohol, N.M.R. in deuteriochloroform: δ2.3 (1H,s), 4.65 (2H,s), 7.2 (2H,d), 7.35 (2H,d).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with diethyl ether
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8a6c4f1d475c48e5b81e3b4d865e66ef
Source dataset
uspto-grants-1991_04
Patent number
US05006543

Reaction notes

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