Sulfuric Acid → rac. 4-Benzyloxy-3-methylbutanal

HRID 1390901Notes

Reaction equation

HRID 1390901 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:14])[CH2:11][C:12]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)=[O:26].[Cl-].[NH4+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([O:8][CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 8025Ethyl formateHCID 25517Ammonium ChlorideHCID 109762734-(Benzyloxy)-3-methylbutanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14658350rac. 4-Benzyloxy-3-methylbutanal

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of 5.8 g. (0.0307 mole) of rac. 4-benzyloxy-3-methylbutyronitrile in 290 ml. of hexane was stirred at -65° C. to -70° C. while 22.4 ml. (4.78 g.; 0.0337 mole) of 25% diisobutylaluminum hydride solution in toluene was added dropwise. The resulting solution was stirred at -65° C. to -70° C. for 0.5 hours then at room temperature for 5 hours whereupon 2.8 ml. of ethyl formate was added dropwise. The reaction mixture was then treated with 250 ml. of saturated aqueous ammonium chloride solution. Stirring was continued for 20 minutes at which point 125 ml. of 5% by weight aqueous sulfuric acid was added and stirring was continued for an additional 10 minutes. The organic layer was separated and the aqueous layer was extracted with ether. The organic solutions were combined and processed as in Example 1 giving 4.79 g. (81.3%) of rac. 4-benzyloxy-3-methylbutanal as a yellow oil.

Workup

  1. waitat room temperature for 5 hours whereupon 2.8 ml
  2. additionThe reaction mixture was then treated with 250 ml
  3. stirringStirring
  4. waitwas continued for 20 minutes at which
  5. stirringstirring
  6. waitwas continued for an additional 10 minutes
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with ether

Sources & evidence

ORD record
ord-9bb9c4a4d7b2432c99f0fdd6c31d255c
Source dataset
uspto-grants-1979_02
Patent number
US04140723

Reaction notes

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