Acetic Anhydride → HCID 13748711, compound

HRID 35511Notes

Reaction equation

HRID 35511 reaction equation
[C:1]([C:10]1[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:20](OC(=O)C)(=[O:22])[CH3:21]>S(=O)(=O)(O)O>[C:20]([O:19][C:13]1[CH:12]=[CH:11][C:10]([C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9838158n-Octanoyl-5-salicylic acid

Product 1

HCID 13748711HCID 13748711, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
100 °C

Procedure

1 g of 5-n-octanoylsalicylic acid is suspended in 15 ml of acetic anhydride. After addition of 2 drops of concentrated sulphuric acid the solution is heated to 100° C. for 15 minutes. The solution is poured onto 150 ml of crushed ice. After extracting with ether, washing the organic phase with the water, drying over sodium sulphate and evaporating, 1 g of a white crystalline product is obtained. The yield is 85%. The recrystallization is done from a 50/50 mixture of toluene and petroleum ether. The melting point is 130° C.

Workup

  1. extractionAfter extracting with ether
  2. washwashing the organic phase with the water
  3. dry with materialdrying over sodium sulphate
  4. customevaporating

Sources & evidence

ORD record
ord-e0d9c3e797274338918fac221ca31bcc
Source dataset
uspto-grants-1988_08
Patent number
US04767750

Reaction notes

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