Sodium Chloride → 3-Methoxybenzyl alcohol

HRID 973183Notes

Reaction equation

HRID 973183 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 114613-Methoxybenzoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 814373-Methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 50 g. of m-methoxybenzoic acid in 500 ml. of dry tetrahydrofuran is slowly added to a stirred solution of 15 g. of lithium aluminum hydride in 100 ml. of tetrahydrofuran. When the addition is complete the reaction mixture is refluxed for 1 hour, cooled and then treated with 50 ml. of saturated sodium chloride solution. The resultant slurry is filtered and the insoluble material washed with 200 ml. of ether. The combined filtrates are evaporated to dryness to yield an oil which is distilled under reduced pressure, to yield m-methoxybenzyl alcohol as a colourless oil; I.R.: νmax/film 3630 cm-1.

Workup

  1. additionWhen the addition
  2. temperatureis refluxed for 1 hour
  3. temperaturecooled
  4. additiontreated with 50 ml
  5. filtrationThe resultant slurry is filtered
  6. washthe insoluble material washed with 200 ml
  7. customThe combined filtrates are evaporated to dryness
  8. customto yield an oil which
  9. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-23e8326e289e45228674fc804c9093f4
Source dataset
uspto-grants-1977_10
Patent number
US04055574

Reaction notes

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