Hydrochloric Acid → HCID 67717823, compound

HRID 742459Notes

Reaction equation

HRID 742459 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:11])C)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+].Cl.[CH3:15]O>>[CH3:1][O:2][C:3]1[CH2:4][C:5]([CH3:15])([CH:6]=[CH:7][CH:8]=1)[CH2:9][OH:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 114603-MethoxyacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 67717823HCID 67717823, compoundYield 94%

Procedure

To m-methoxyacetophenone (100 g, 0.665 mol) in 400 mL of methanol was added with cooling sodium borohydride (30.22 g, 0.799 mol) over a period of 1 h and the mixture was stirred, poured into ice-water, and neutralized with conc. HCl. The above mixture was extracted with ether (3×400 mL), the organic layer was dried over sodium sulfate, and concentrated. The residue was then distilled (149°-151° C. @ 25 mm)(short path column) to afford 95.6 g (94%) of m-methoxy-1-methyl-benzyl alcohol as a clear oil.

Workup

  1. extractionThe above mixture was extracted with ether (3×400 mL)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. distillationThe residue was then distilled (149°-151° C. @ 25 mm)(short path column)

Sources & evidence

ORD record
ord-cc20dd2351844ccb8a09b24c0c1c5d5a
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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