Benzyl Bromide → p-(Benzyloxy)phenethyl alcohol

HRID 649202Notes

Reaction equation

HRID 649202 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1.[Na].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1.O.CCCCCC>[CH2:14]([O:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 10393TyrosolHCID 24758Sodium hydrideHCID 5360545Sodium

Product 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

NaH (1.42 g of 60% in oil, 0.036 mol) was washed 2×5 ml hexane and then suspended in tetrahydrofuran (20 ml). 4-Hydroxyphenethyl alcohol (5.0 g, 0.036 mol) was added portionwise and the mixture stirred for 20 minutes to assure complete conversion to the sodium salt. Benzyl bromide (4.2 ml, 1 equivalent) was added and the resulting mixture refluxed for 4 hours, then poured into 50 ml H2O and extracted 3×50 ml ether. The organic layers were combined, extracted 2×20 ml 1N NaOH and then 2×20 ml H2O, dried (MgSO4), stripped, and the solid residue recrystallized from ethyl acetate and cyclohexane to yield title product 4.4 g.

Workup

  1. temperaturethe resulting mixture refluxed for 4 hours
  2. extractionextracted 3×50 ml ether
  3. extractionextracted 2×20 ml 1N NaOH
  4. dry with material2×20 ml H2O, dried (MgSO4)
  5. customthe solid residue recrystallized from ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-cd990a11e01a47e8b692505dc1cf5688
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Reaction notes

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