1-(4-Chlorophenyl)-2-methoxyethanone → 1-(4-Chlorophenyl)-2-methoxy-ethan-1-ol

HRID 2177014

Reaction equation

HRID 2177014 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH2:11][O:12][CH3:13])=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:14])[CH2:11][O:12][CH3:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3184091-(4-Chlorophenyl)-2-methoxyethanoneHCID 4311764Sodium borohydride

Product 1

HCID 615532221-(4-Chlorophenyl)-2-methoxy-ethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (111 mg, 2.9 mmol) was added in portions to a solution of 1-(4-chlorophenyl)-2-methoxy-ethanone (1 g, 6.4 mmol) in methanol at room temperature. After 1 hour, reaction was quenched with 3 mls (aq) sat. NH4Cl. Water was added to dissolve the inorganic and mixture was extracted with ethyl acetate 3×5 ml. Combined organics were washed with brine (2×3 ml) and dried over MgSO4. Crude material was obtained upon filtration and concentration to an amber oil which was purified by flash silica gel and eluted with 10-17% EA/Hex gradient. 1-(4-chlorophenyl)-2-methoxy-ethan-1-ol was obtained as an amber oil (370 mg, 68% yield).

Workup

  1. customreaction
  2. customwas quenched with 3 mls (aq) sat. NH4Cl
  3. additionWater was added
  4. dissolutionto dissolve the inorganic and mixture
  5. extractionwas extracted with ethyl acetate 3×5 ml
  6. washCombined organics were washed with brine (2×3 ml)
  7. dry with materialdried over MgSO4
  8. customCrude material was obtained upon filtration and concentration to an amber oil which
  9. customwas purified by flash silica gel
  10. washeluted with 10-17% EA/Hex gradient

Sources & evidence

ORD record
ord-2308c14a87ee4e2fb4976f0f4432c1cb
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Linked notes

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