1-Octanol → Octyl acetoacetate

HRID 729110Notes

Reaction equation

HRID 729110 reaction equation
[CH3:1][C:2]([CH2:4][C:5]([O:7][C:8]([CH3:11])(C)C)=[O:6])=[O:3].[CH2:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]CC.C1(C)C=CC=CC=1>C(O)(C)(C)C>[C:5]([O:7][CH2:8][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:6])[CH2:4][C:2]([CH3:1])=[O:3]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 1140TolueneHCID 15538Tert-butyl acetoacetate2×

Product 1

HCID 85418Octyl acetoacetateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Another procedure involved heating the alcohol and tBAA, (or beta-ketoester) in solvent, in a round-bottom flask with magnetic stirrer,5-plate Oldershaw column and still head for removal of the t-butanol co-product. For example: a solution of n-octanol (13 g, 0.1 mol), tBAA (16.6 g, 0.105 mol) and 50 mL toluene was heated at reflux until the theoretical amount of t-butyl alcohol was obtained (ca. 15 min. after reflux). The reaction mixture was subsequently concentrated and distilled to give 17.8 g (83.2%) octyl acetoacetate b.p. 95-110° C. (1.0 mm Hg).

Workup

  1. customin a round-bottom flask with magnetic stirrer,5-plate Oldershaw column and still head for removal of the t-butanol co-product
  2. customwas obtained
  3. temperature(ca. 15 min. after reflux)
  4. concentrationThe reaction mixture was subsequently concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-28ba4201c247479fa881c5fa6d079b96
Source dataset
uspto-grants-1991_09
Patent number
US05051529

Reaction notes

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