Diisopropyl Ether → 6-bromohexyl Acetate

HRID 1092898Notes

Reaction equation

HRID 1092898 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].C(OC(C)C)(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 779706-Bromo-1-hexanol

Product 1

HCID 118062916-bromohexyl AcetateYield 96.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

20.1 g (0.16 mol) of DMAP were added to 297.4 g (1.64 mol) of 6-bromo-1-hexanol in 1500 ml of THF. A solution of 184.4 g (1.81 mol) of acetic anhydride in 300 ml of THF was added dropwise in such a way that the reaction temperature did not exceed 30° C. After completion of the addition, the mixture was stirred for a further 30 minutes. The reaction mixture was mixed with 500 ml of diisopropyl ether and extracted successively with 700 ml each of water, 2× saturated NaHCO3 solution and water. After drying over sodium sulfate, the solvent was removed in vacuo. 352.8 g (1.58 mol, 96%) of 6-bromohexyl acetate were obtained.

Workup

  1. customdid not exceed 30° C
  2. additionAfter completion of the addition
  3. extractionextracted successively with 700 ml each of water, 2× saturated NaHCO3 solution and water
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e1caca37c0ed4c72acdaa28ecd4375a0
Source dataset
uspto-grants-2012_03
Patent number
US08129552B2

Reaction notes

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