Acetic Anhydride → 2-Methyl-6-acetamidobenzyl alcohol

HRID 2073795Notes

Reaction equation

HRID 2073795 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][OH:5].[C:11](OC(=O)C)(=[O:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH:1][C:11](=[O:13])[CH3:12])[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 15339417(2-Amino-6-methylphenyl)methanol

Product 1

HCID 143684642-Methyl-6-acetamidobenzyl alcoholYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-amino-6-methylbenzyl alcohol (30 g) in methylene chloride (300 ml) was added dropwise acetic anhydride (22.3 g) at 5° to 10° C. After being stirred for 3 hours, the mixture was neutralized with sodium bicarbonate aqueous solution to give precipitates. To said mixture was added chloroform to dissolve said precipitates and then the organic layer was washed with water and sodium chloride aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The resultant residue was suspended in diethyl ether and the precipitates were collected by filtration to give 2-methyl-6-acetamidobenzyl alcohol (25.30 g).

Workup

  1. customto give
  2. customprecipitates
  3. additionwas added chloroform
  4. dissolutionto dissolve
  5. customsaid precipitates
  6. washthe organic layer was washed with water and sodium chloride aqueous solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-a80899f975f149b7b0505acf426b856d
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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