Acetic Anhydride → HCID 69953517, compound

HRID 1979250Notes

Reaction equation

HRID 1979250 reaction equation
[CH:1]1([CH2:7]/[CH:8]=[CH:9]/[CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(N(CC)CC)C>C(OCC)C.CN(C)C1C=CN=CC=1>[C:12]([O:11][CH2:10]/[CH:9]=[CH:8]/[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11062610HCID 11062610, compound

Product 1

HCID 69953517HCID 69953517, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.54 g of (E)-4-cyclohexyl-2-butenol in 200 ml of diethyl ether was treated with 9.99 g of acetic anhydride and 7.42 g of triethylamine and stirred overnight at room temperature. The mixture was then treated with 0.005 g of 4-dimethylaminopyridine and stirred for a further 0.5 hours. The mixture was washed with 5% aqueous sodium hydrogen carbonate, water and brine, then dried over anhydrous magnesium sulphate and evaporated. The residue was dried under vacuum to give 9.50 g of (E)-4-cyclohexyl-2-butenol acetate in the form of a pale yellow oil.

Workup

  1. stirringstirred for a further 0.5 hours
  2. washThe mixture was washed with 5% aqueous sodium hydrogen carbonate, water and brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-dec47038f1bb4042ae30e8de6dbe7e92
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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