4-Benzyloxy-2-hydroxybenzaldehyde → 5-Benzyloxy-2-hydroxymethylphenol

HRID 1044443Notes

Reaction equation

HRID 1044443 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:17])[C:12](=[CH:15][CH:16]=1)[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 251384215-Benzyloxy-2-hydroxymethylphenolYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled suspension of 4-benzyloxy-2-hydroxy-benzaldehyde (0.228 g, 1 mmol) in 10 mL of methanol was slowly added sodium borohydride (0.038 g, 1 mmol). After addition of sodium borohydride, a clear solution was obtained. The reaction was stirred at 0° C. for 20 minutes followed by stirring at RT for 10 minutes. The solvent was evaporated under vacuum. To this solid residue was carefully added 0.1 N H2SO4 until the pH dropped to 6.5 with vigorous stirring. Additional water (ca. 40 mL) was added with continuous stirring which then caused the product to precipitate. The solid was filtered and copiously washed with water to remove all traces of acid (last wash pH>7). The solid was immediately vacuum dried to obtain 0.175 g (76%) white solid: mp 88-90° C.; TLC, Rf0.29, in hexanes:EtOAc (2:1); 1H NMR (600 MHz, DMSO-d6) δ, 9.36 (s, 1H, Ph-OH), 7.43-7.32 (m, 5H, C6H5), 7.14-7.12 (d, 1H, J=8.4 Hz, Ar—H6), 6.44-6.41 (m, 2H, Ar—H5/Ar—H3), 5.01 (s, 2H, PhCH2), 4.8 (t, 1H, CH2OH), 4.39 (s, 2H, CH2OH); 13C NMR (100 MHz, DMSO-d6) δ 158.0, 155.2, 137.3, 128.5, 128.4, 128.3, 127.6, 127.5, 127.3, 121.2, 104.8, 101.8, 68.9, 57.9; analysis calcd. for C14H14O3. C, 73.03; H, 6.13. found: C, 73.16; H, 5.94.

Workup

  1. customa clear solution was obtained
  2. stirringby stirring at RT for 10 minutes
  3. customThe solvent was evaporated under vacuum
  4. additiondropped to 6.5 with vigorous stirring
  5. additionAdditional water (ca. 40 mL) was added
  6. stirringwith continuous stirring which
  7. customto precipitate
  8. filtrationThe solid was filtered
  9. washcopiously washed with water
  10. customto remove
  11. washall traces of acid (last wash pH>7)
  12. customdried

Sources & evidence

ORD record
ord-c8c04b8275c44e3187f8e2cd18390838
Source dataset
uspto-grants-2013_10
Patent number
US08563599B2

Reaction notes

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