Acetic Anhydride → HCID 20386054, compound

HRID 46980Notes

Reaction equation

HRID 46980 reaction equation
[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(OCC)C>[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 203860504-(4-Acetyl-8-hydroxytridecyl)benzoic acid

Product 1

HCID 20386054HCID 20386054, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(4-acetyl-8-hydroxytridecyl)benzoic acid (9.0 g., 0.025 mole) and acetic anhydride (6.1 g., 0.06 mole) is heated at 60° C. for 18 hours. The mixture is then cooled and dissolved in 80 ml. ethyl ether. The solution is extracted with an ice-cold solution of 8 g. sodium hydroxide in 150 ml. water. The basic solution is separated and acidified with concentrated hydrochloric acid. The oily acid which separates is taken up in ether, washed with water, and dried over sodium sulfate. The ether is evaporated to leave the oily crude product.

Workup

  1. temperatureThe mixture is then cooled
  2. dissolutiondissolved in 80 ml
  3. extractionThe solution is extracted with an ice-cold solution of 8 g
  4. customThe basic solution is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe ether is evaporated

Sources & evidence

ORD record
ord-f34416ec30ab49868372cd26a6976fe5
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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