Triethylamine → Ethyl 4-butyrylbenzoate

HRID 1424242Notes

Reaction equation

HRID 1424242 reaction equation
[OH:1][CH:2]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].C(N(CC)CC)C>ClCCl.CS(C)=O>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=1)(=[O:1])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67981039Ethyl 4-(1-hydroxybutyl)benzoate

Product 1

HCID 67980577Ethyl 4-butyrylbenzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the crude alcohol (1.0 g, 4.5 mmol) in dichloromethane (16.7 mL), dimethylsulfoxide (4.79 mL) and triethylamine (2.28 g, 22.5 mmol) was cooled to 0° C. Sulfur trioxide pyridine complex (2.15 g, 13.5 mmol) was added in portions and the mixture stirred at 0° C. for 1 hour. The reaction was then allowed to warm to room temperature and stir for 2 hours. The reaction was quenched with brine and diluted with dichloromethane. The layers were separated and the aqueous was extracted again with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-30% ethyl acetate in heptane) gave ethyl 4-butyrylbenzoate (Intermediate 1). 1H NMR (400 MHz, CDCl3) δ 8.05-8.17 (m, 2H), 8.04-7.92 (m, 2H), 4.40 (q, J=7.15 Hz, 2H), 2.96 (t, J=7.22 Hz, 2H), 1.86-1.69 (m, 2H), 1.40 (t, J=7.12 Hz, 3H), 1.00 (t, J=7.22 Hz, 3H).

Workup

  1. additionSulfur trioxide pyridine complex (2.15 g, 13.5 mmol) was added in portions
  2. temperatureto warm to room temperature
  3. stirringstir for 2 hours
  4. customThe reaction was quenched with brine
  5. additiondiluted with dichloromethane
  6. customThe layers were separated
  7. extractionthe aqueous was extracted again with dichloromethane
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by column chromatography (0-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f404bb61c109453b9a974f935b5b7e95
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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