Hydrochloric Acid → 5-(Benzyloxy)-2-methylphenol

HRID 2426120Notes

Reaction equation

HRID 2426120 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH3:13])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 575815905-(Benzyloxy)-2-methylphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-2-hydroxybenzaldehyde (2.28 g, 10.0 mmol, prepared by the method of Example 18 below) and sodium cyanoborohydride (2.0 g, 15.9 mmol) in tetrahydrofuran (60 mL) was added methyl orange as an indicator, giving the solution a yellow color; 1N aqueous HCl solution (15 mL) was added slowly, keeping the solution orange. The mixture was stirred overnight at room temperature. Water was added, and the mixture was extracted with ethyl acetate three times. The combined organic phase was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 0-40% ethyl acetate in hexanes to give 5-benzyloxy-2-methyl-phenol. (Yield 0.64 g).

Workup

  1. customgiving the solution a yellow color
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ed65d58f77df4e35b7b40d1b9ab340a1
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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