Aluminium lithium hydride → 2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3-(1-hydroxymethylethoxy)-4-nitrophenyl ether

HRID 2291423Notes

Reaction equation

HRID 2291423 reaction equation
[Cl:1][C:2]1[CH:7]([O:8][CH:9]([C:11](OCC)=[O:12])[CH3:10])[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])([N+:16]([O-:18])=[O:17])[CH:5]=[CH:4][C:3]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:46]([O-:48])=[O:47])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:45])([F:44])[F:43])[CH:32]([O:49][CH:50]([C:52](OCC)=[O:53])[CH3:51])[C:31]=1[Cl:57].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Cl:1][C:2]1[CH:7]([O:8][CH:9]([CH2:11][OH:12])[CH3:10])[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:26])([F:28])[F:27])([N+:16]([O-:18])=[O:17])[CH:5]=[CH:4][C:3]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:46]([O-:48])=[O:47])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:44])([F:43])[F:45])[CH:32]([O:49][CH:50]([CH2:52][OH:53])[CH3:51])[C:31]=1[Cl:57]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 867350572-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3-(1-carbethoxyethoxy)-4-nitrophenyl ether

Product 1

HCID 867357482-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3-(1-hydroxymethylethoxy)-4-nitrophenyl ether

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-carbethoxyethoxy)-4-nitrophenyl ether (17.32 g, 0.04 mole) in dry ether (500 ml) is treated at -10° C. with a suspension of lithium aluminum hydride (1.9 g) in ether (approximately) 100 ml) added with stirring over ten seconds. The temperature increases to about 0° to 10° C. and after a total of 45 seconds, the reaction mixture is quenched by pouring, with stirring, onto ice/dilute sulfuric acid. The ether phase is washed with water, dried, filtered through activated silica gel, and the solvent removed to give 2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-hydroxymethylethoxy)-4-nitrophenyl ether as a dark oil, yield 14 g.

Workup

  1. additionadded
  2. temperatureThe temperature increases to about 0° to 10° C.
  3. customafter a total of 45 seconds, the reaction mixture is quenched
  4. additionby pouring
  5. stirringwith stirring, onto ice/dilute sulfuric acid
  6. washThe ether phase is washed with water
  7. customdried
  8. filtrationfiltered through activated silica gel
  9. customthe solvent removed

Sources & evidence

ORD record
ord-f8f00d8b458a4db8adab2a7b478fb5c9
Source dataset
uspto-grants-1989_01
Patent number
US04795825

Reaction notes

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