HCID 14519881, compound → 4-Methyl-2-(phenylmethoxy)benzenemethanol

HRID 1198625Notes

Reaction equation

HRID 1198625 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1>S(Cl)(Cl)=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

3

Reactant 1

HCID 14519881HCID 14519881, compound

Product 1

HCID 8186924-Methyl-2-(phenylmethoxy)benzenemethanolYield 93.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst

Procedure

A solution of 4-methyl-2-phenylmethoxy-benzoic acid (30.3 g, 0.125 mol) in 100 ml thionyl chloride containing 3 drops DMF was heated under reflux for 30 min. The SOCl2 was removed under vacuum and the residual oil was diluted with 100 ml dry benzene. The solvent was again removed under vacuum to remove remaining traces of SOCl2 and the crude acid chloride product was added slowly to a solution of NaBH4 (10 g) in dry diglyme (200 ml) at 10°-20° C. The resulting mixture was stirred for 30 min at room temperature and the solvent was removed under vacuum by heating in an oilbath. Water (100 ml) was added slowly to the white solid and then acetic acid (10 ml) was added to ensure complete decomposition of the excess borohydride. The mixture was basified with conc. ammonia and extracted with ethyl acetate to give 4-methyl-2-phenylmethoxybenzenemethanol (26.6 g, 93% crude yield) as an oil.

Workup

  1. temperatureunder reflux for 30 min
  2. customThe SOCl2 was removed under vacuum
  3. additionthe residual oil was diluted with 100 ml dry benzene
  4. customThe solvent was again removed under vacuum
  5. customto remove
  6. additionthe crude acid chloride product was added slowly to a solution of NaBH4 (10 g) in dry diglyme (200 ml) at 10°-20° C
  7. customthe solvent was removed under vacuum
  8. temperatureby heating in an oilbath
  9. additionWater (100 ml) was added slowly to the white solid
  10. additionacetic acid (10 ml) was added
  11. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-07db7284a4c14c75b16a7955b834c3cf
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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