Acetic Anhydride → HCID 20062797, compound

HRID 2166156Notes

Reaction equation

HRID 2166156 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Mg].[C:16](OC(=O)C)(=[O:18])[CH3:17].[Cl-].[NH4+]>CCOCC>[C:9]1([CH2:8][CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:2][C:16](=[O:18])[CH3:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19798052HCID 19798052, compound

Product 1

HCID 20062797HCID 20062797, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

[2-(4-Bromobutoxy)ethyl]benzene (10.0 g) in dry ether (80 ml) was added dropwise to magnesium turnings (0.946 g) under nitrogen with stirring to give a gentle reflux. The reaction mixture was refluxed for 1 h, allowed to cool to room temperature and added dropwise to acetic anhydride (8.07 g) in dry ether (55 ml) at -70° under nitrogen with stirring over 1.5 h. The reaction mixture was stirred at -70° for 2 h, allowed to warm to -10° , then treated with saturated ammonium chloride (100 ml). The organic layer was separated and the aqueous layer re-extracted with ER (150 ml). The combined organic extracts were washed with 2N aqueous sodium hydroxide (150 ml), brine (150 ml), dried and evaporated to give an oil (7.54 g) which was purified by FCC eluting with ER-CX (1:3) to give the title compound as a colourless oil (4.34 g). T.l.c. (ER-CX 1:3) Rf 0.25.

Workup

  1. customto give a gentle reflux
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. stirringwith stirring over 1.5 h
  4. stirringThe reaction mixture was stirred at -70° for 2 h
  5. temperatureto warm to -10°
  6. customThe organic layer was separated
  7. extractionthe aqueous layer re-extracted with ER (150 ml)
  8. washThe combined organic extracts were washed with 2N aqueous sodium hydroxide (150 ml), brine (150 ml)
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-02782ddb1ea54776bd44fa901cc1f454
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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