Acetic Anhydride → HCID 87833005, compound

HRID 868775Notes

Reaction equation

HRID 868775 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:5])[C:2]([CH3:4])=[O:3].[C:15](OC(=O)C)(=[O:17])[CH3:16]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C>[C:15]([O:3][C:2](=[CH2:4])[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:5])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 12422202Octyl 2-oxopropanoate

Product 1

HCID 87833005HCID 87833005, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Next, in a mixture of the obtained octyl pyruvate (300 g, 1.5 mol) and acetic anhydride (306 g, 3.0 mol), p-toluenesulfonic acid monohydrate (5 g) was added. Then, the mixture was stirred under a nitrogen gas stream at 120° C. for 27 hours, thereby obtaining a second reaction solution. Next, acetic acid generated by a reaction with excess acetic anhydride under reduced pressure (5 mmHg) was removed from the second reaction solution. Thereafter, the residue was purified by reduced pressure distillation (1 mmHg or less, 80 to 102° C.), thereby obtaining octyl α-acetoxyacrylate (215 g, yield 59%).

Workup

  1. additionwas added
  2. customobtaining a second reaction solution
  3. customwas removed from the second reaction solution
  4. distillationThereafter, the residue was purified by reduced pressure distillation (1 mmHg or less, 80 to 102° C.)

Sources & evidence

ORD record
ord-506a9d03aa8d4c378f44e32d1cb45819
Source dataset
uspto-grants-2015_03
Patent number
US08968975B2

Reaction notes

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