Benzyl Bromide → 6-Benzyloxy-1-hexanol

HRID 704552Notes

Reaction equation

HRID 704552 reaction equation
CC(C)([O-:4])C.[K+].[CH:7]([OH:14])(O)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH2:15]([O:4][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][OH:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 147023HexanediolHCID 23665647Potassium tert-butoxide

Product 1

HCID 27847636-Benzyloxy-1-hexanolYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pure potassium t-butoxide (50 mmoles, 5.61 g) is added portionwise to a stirred solution of 100 mmoles of hexanediol (11.82 gr) dissolved in 30 ml of THF at room temperature under argon. When addition is complete, 50 mmoles of benzylbromide (5.9 ml) are introduced and the reaction mixture is stirred at room temperature overnight. The white solid is then removed by filtration, the filtrate is evaporated and the residue is dissolved in ethylacetate, washed with saturated ammonium chloride, H2O and brine. Usual workup and purification by flash chromatography gives finally 7.51 g of product (72%).

Workup

  1. additionWhen addition
  2. customThe white solid is then removed by filtration
  3. customthe filtrate is evaporated
  4. dissolutionthe residue is dissolved in ethylacetate
  5. washwashed with saturated ammonium chloride, H2O and brine
  6. customUsual workup and purification by flash chromatography

Sources & evidence

ORD record
ord-77dcd2851cee4ee88a5b0d3fe48a05a8
Source dataset
uspto-grants-1991_01
Patent number
US04988680

Reaction notes

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