Benzyl Bromide → 2-(4-Benzyloxy-3-methoxy-phenyl)-ethanol

HRID 506863Notes

Reaction equation

HRID 506863 reaction equation
[CH2:1]([OH:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>C(O)C>[CH2:13]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH2:2][CH2:1][OH:12])=[CH:4][C:5]=1[O:6][CH3:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 16928Homovanillyl alcohol

Product 1

HCID 5636982-(4-Benzyloxy-3-methoxy-phenyl)-ethanolYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of homovanillyl alcohol (100 mmol, 17.0 g), benzyl bromide (105 mmol, 18.33 g) and 5M aqueous NaOH (24 mL) in ethanol (200 mL) was refluxed for 6 h. The organic solvent was evaporated in vacuo. The residue was partitioned between brine (200 mL) and diethyl ether (200 mL). The aqueous layer was separated from the organic layer and extracted again with ether. The combined organic layers were dried over MgSO4 and the solvent was evaporated in vacuo. Purification by dry-column chromatography with mixtures of ethyl acetate-hexanes (1:4, 1:3, v/v) yielded 20.66 g (80% yield) of (DC-61) as pale yellow oil. Rf 0.25 (EtOAc-hexanes, 1:1, v/v); 1H-NMR (300 MHz, CDCl3) δ 7.44-7.25 (m, 5H, Ar), 6.84-6.67 (m, 3H, Ar), 5.12 (s, 2H, PhCH2O), 3.88 (s, 3H, CH3O), 3.81 (t, 2H, CH2CH2OH), 2.79 (t, 2H, CH2CH2OH), 1.54 (s, 1H, OH); 13C-NMR (75 MHz, CDCl3, APT) δ 149.63 (+), 146.75 (+), 137.21 (+), 131.60 (+), 128.43 (−), 127.70 (−), 127.17 (−), 120.84 (−), 114.25 (−), 112.74 (−), 71.07 (+), 63.58 (+), 55.90 (−), 38.67 (+).

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe organic solvent was evaporated in vacuo
  3. customThe residue was partitioned between brine (200 mL) and diethyl ether (200 mL)
  4. customThe aqueous layer was separated from the organic layer
  5. extractionextracted again with ether
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customthe solvent was evaporated in vacuo
  8. customPurification by dry-column chromatography with mixtures of ethyl acetate-hexanes (1:4, 1:3
  9. customv/v) yielded 20.66 g (80% yield) of (DC-61) as pale yellow oil

Sources & evidence

ORD record
ord-7aaadf052c854f63b88a58a0691e555f
Source dataset
uspto-grants-2010_08
Patent number
US07786119B2

Reaction notes

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