Benzyl Bromide → 6-Benzyloxy-1-hexanol

HRID 530275Notes

Reaction equation

HRID 530275 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[H-].[Na+].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1>C1COCC1>[CH2:17]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:8])[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 123741,6-HexanediolHCID 24758Sodium hydride

Product 1

HCID 27847636-Benzyloxy-1-hexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,6-hexan-diol in dry THF at 0° C., NaH (1.1 equiv) was added. After stirring for 30 min, BnBr (1 equiv) was added slowly dropwise using a syringe and stirred for additional 3 h. After completion of the reaction (monitored by TLC), it was quenched with ice and the organic layer was extracted using ether and washed with brine and dried over anhydrous Na2SO4. The solvent was removed in vacuum and concentrated. The crude was purified by chromatographic technique (EtOAc:pet ether=20:80). 1H NMR (CDCl3, 200 MHz) δ 7.3-7.4 (5H, m), 4.5 (s, 2H), 3.6 (t, 2H), 3.4 (t, 2H), 1.8 (br s, 1H), 1.6 (m, 4H), 1.4 (m, 4H); 13C NMR (CDCl3, 50 MHz): 138.56, 128.34, 127.62, 127.50, 72.87, 70.29, 62.63, 32.67, 29.73, 26.03, 25.62

Workup

  1. stirringstirred for additional 3 h
  2. customAfter completion of the reaction (monitored by TLC), it
  3. customwas quenched with ice
  4. extractionthe organic layer was extracted
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed in vacuum
  8. concentrationconcentrated
  9. customThe crude was purified by chromatographic technique (EtOAc:pet ether=20:80)

Sources & evidence

ORD record
ord-8d10734d673e4c8ca7f9188fb9206921
Source dataset
uspto-grants-2016_05
Patent number
US09353077B2

Reaction notes

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