Tetrahydrofuran → 2-(8-Phenyloctyl)benzaldehyde

HRID 2258280Notes

Reaction equation

HRID 2258280 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=NC(C)(C)C.CC1(C)CCCC(C)(C)N1.[Li]CCCC.Cl[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[O:43]1CCCC1>>[C:37]1([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH:1]=[O:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 130352,2,6,6-TetramethylpiperidineHCID 5224107-Phenyl-1-heptyl chlorideHCID 10866848HCID 10866848, compoundHCID 178418339Butyllithium

Product 1

HCID 98176132-(8-Phenyloctyl)benzaldehyde

Conditions

Temperature
40 °C

Procedure

A stirred solution of N-[(2-methylphenyl)methylene]-1,1-dimethylethanamine (11.2 g, 0.064 mol) and 2,2,6,6-tetra-methylpiperidine (0.9 g, 0.0064 mol) in tetrahydrofuran (40 mL) was cooled to -5° C. To this was added n-BuLi (1.6M, 40 mL, 0.064 mol) over 60 min from a syringe pump such that the temperature was maintained below 0° C. The mixture was stirred for 30 min and 1-chloro-7-phenylheptane (11.23 g, 0.053 mol) in tetrahydrofuran (20 mL) quickly added. The reaction mixture was heated at 50°-55° C. for 2 h. The reaction mixture was cooled to 40° C. and quenched by the slow addition of dilute hydrochloric acid (100 mL of acid diluted with 300 mL of water). Hydrolysis was completed by heating the mixture at 50°-60° C. for 2.5 h. The mixture was cooled to ambient temperature and the organic phase separated. The aqueous phase was extracted with hexane (100 mL) and the combined organic extracts washed with water (100 mL). The extracts were dried over magnesium sulphate and after filtering and washing the filter cake with hexane the organic solution was concentrated under vacuum to give 2-(8-phenyloctyl)benzaldehyde as an oil (14.5 g, 69.3% pure by HPLC assay, 87% corrected yield).

Workup

  1. temperaturewas maintained below 0° C
  2. temperatureThe reaction mixture was heated at 50°-55° C. for 2 h
  3. customquenched by the slow addition of dilute hydrochloric acid (100 mL of acid diluted with 300 mL of water)
  4. customHydrolysis
  5. temperatureby heating the mixture at 50°-60° C. for 2.5 h
  6. temperatureThe mixture was cooled to ambient temperature
  7. customthe organic phase separated
  8. extractionThe aqueous phase was extracted with hexane (100 mL)
  9. washthe combined organic extracts washed with water (100 mL)
  10. dry with materialThe extracts were dried over magnesium sulphate
  11. filtrationafter filtering
  12. washwashing the filter cake with hexane the organic solution
  13. concentrationwas concentrated under vacuum
  14. customto give

Sources & evidence

ORD record
ord-32f2c1f159464757a27990ec022d3274
Source dataset
uspto-grants-1997_08
Patent number
US05659084

Reaction notes

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