Hydrochloric Acid → 2-Methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethanol

HRID 1638308Notes

Reaction equation

HRID 1638308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([F:23])[CH:22]=1)[O:5][C:6]1[CH:19]=[CH:18][C:9]([O:10][CH:11]([CH3:17])[C:12](OCC)=[O:13])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)C>[CH3:17][CH:11]([O:10][C:9]1[CH:18]=[CH:19][C:6]([O:5][C:4]2[CH:20]=[C:21]([F:23])[CH:22]=[C:2]([F:1])[CH:3]=2)=[CH:7][CH:8]=1)[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15671702HCID 15671702, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 134559122-Methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethanolYield 92.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The thus obtained ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]propionate (15.6 g) was dissovled in diethyl ether (10 ml). The resulting solution was dropwise added to a suspension of lithium aluminum hydride (1.38 g, 36.3 mmol) in diethyl ether (70 ml) with stirring at an inner temperature of -20° to -10° C. After completion of the addition, stirring was continued for 1 hour while keeping the inner temperature at 0° to 5° C. The reaction mixture was poured into a mixture of ice and hydrochloric acid and extracted with ether. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was removed to give 2-methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethanol (12.6 g).

Workup

  1. additionAfter completion of the addition
  2. stirringstirring
  3. customat 0° to 5° C
  4. extractionextracted with ether
  5. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-e266b0fd98704a50b3ce714ec8009d11
Source dataset
uspto-grants-1989_11
Patent number
US04879292

Reaction notes

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