Sulfuric Acid → (+/-)-2-Cyano-4-(2,5-diacetoxy-3,4,6-trimethylphenyl)butan-2-ol

HRID 2399061Notes

Reaction equation

HRID 2399061 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C:20](=[O:22])[CH3:21])(=[O:3])[CH3:2].C[N:24]([CH3:27])C=O.[C-]#N.[K+].OS(O)(=O)=O>O>[C:27]([C:20]([OH:22])([CH2:19][CH2:18][C:6]1[C:7]([CH3:17])=[C:8]([O:13][C:14](=[O:16])[CH3:15])[C:9]([CH3:12])=[C:10]([CH3:11])[C:5]=1[O:4][C:1](=[O:3])[CH3:2])[CH3:21])#[N:24]

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 1044132-Butanone, 4-[2,5-bis(acetyloxy)-3,4,6-trimethylphenyl]-

Product 1

HCID 21432286(+/-)-2-Cyano-4-(2,5-diacetoxy-3,4,6-trimethylphenyl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the crude 4-(2,5-diacetoxy-3,4,6-trimethylphenyl) butan-2-one prepared in Example 56 in 963 ml. of dimethylformamide was cooled under N2 in an ice bath. A solution of 69.4 g. of potassium cyanide in 150 ml. of H2O was added over 20 minutes. The mixture was stirred another 10 minutes and then 161 ml. of 6N H2SO4 was added dropwise over 20 minutes while an internal temperature of +10° to +13° was maintained. The viscous suspension (pH 8) was stirred another 30 minutes, brought to pH 4 by the addition of 16.5 ml. of 6N H2SO4, poured into ice-H2O, and extracted with ether. The ether solutions were washed with brine, dried over Na2SO4, and stripped of solvent to give (±)-2-cyano-4-(2,5-diacetoxy-3,4,6-trimethylphenyl)butan-2-ol as an orange-brown foam.

Workup

  1. temperaturewas maintained
  2. additionbrought to pH 4 by the addition of 16.5 ml
  3. extractionextracted with ether
  4. washThe ether solutions were washed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d536e5280b4d4fcf82b6718dd6f60183
Source dataset
uspto-grants-1977_05
Patent number
US04026907

Reaction notes

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