Phenol → 7-(Phenyloxy)-1-heptanol

HRID 2301358Notes

Reaction equation

HRID 2301358 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[C:1]1([O:7][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 662841-Heptanol, 7-bromo-

Product 1

HCID 158562647-(Phenyloxy)-1-heptanolYield 101.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenol (0.098 g, 1.04 mmol) and 7-bromo-1-heptanol (0.243 g, 1.246 mmol) were dissolved in acetone (25 mL) in a 50 mL round bottomed flask. Potassium carbonate (0.86 g, 6.23 mmol) was added to this solution and the flask was fitted with a condenser and refluxed using an oil bath at 70° C. for a period of 26 hours. The reaction flask was then cooled to room temperature. The contents of the flask was then filtered through a fluted filter paper and washed with acetone (10 mL). The combined filtrate was then evaporated to dryress under reduced pressure. The residue obtained was dissolved in ethyl acetate (25 mL). The ethyl acetate solution was then washed with 1N. NaOH (3×5 mL), water (2×5 mL) and brine (2×5 mL). The organic layer was dried over Na2SO4. Removal of solvent from the dried extract under reduced pressure afforded the product. The product was then purified by flash chromatography (Si gel, 12×2.5 cm) using ethyl acetate: hexane (1:1) to afford the pure 7-(phenyloxy)-1-heptanol (0.22 g, quantitative yield). The product alcohol from step A was analyzed yielding the following confirmatory data: 1H-NMR (CDCl3) δ 1.31-1.52 (m, 6H), 1.52-1.63 (m, 2H), 1.73-1.89 (m, 2H), 1.97 (bs, 1H), 3.61 (t, 2H, J=6.57 Hz), 3.93 (t, 2H, J=6.50 Hz), 6.80-6.97 (m, 3H) and 7.20-7.28 (m, 2H); 13C-NMR (CDCl3) δ 25.5, 25.8, 29.0, 29.1, 32.4, 62.5, 67.7, 114.3, 120.3, 129.2 and 158.8; IR (neat): 3348 cm−1; MS (ES+): 209 (M+1).

Workup

  1. customthe flask was fitted with a condenser
  2. temperaturerefluxed
  3. customat 70° C.
  4. customof 26 hours
  5. filtrationThe contents of the flask was then filtered through
  6. filtrationa fluted filter paper
  7. washwashed with acetone (10 mL)
  8. customThe combined filtrate was then evaporated
  9. customThe residue obtained
  10. washThe ethyl acetate solution was then washed with 1N
  11. dry with materialThe organic layer was dried over Na2SO4
  12. customRemoval of solvent from the dried
  13. extractionextract under reduced pressure
  14. customafforded the product
  15. customThe product was then purified by flash chromatography (Si gel, 12×2.5 cm)

Sources & evidence

ORD record
ord-17d0bc22e1e941a096e1c24bd3783998
Source dataset
uspto-grants-2002_12
Patent number
US06500852B1

Reaction notes

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