Methanol → (2,3-Dihydro-1,4-benzodioxin-2-yl)acetaldehyde

HRID 1391065Notes

Reaction equation

HRID 1391065 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][C:12]#N.[H-].C([Al+]CC(C)C)C(C)C.C[OH:25].O>C1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][CH:12]=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2675312-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 21331989(2,3-Dihydro-1,4-benzodioxin-2-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The starting material is prepared as follows: To the solution of 20 g of 1,4-benzodioxan-2-yl-acetonitrile in 200 ml of benzene is added dropwise 71 ml of a 1.6 N solution of diisobutyl aluminum hydride in benzene while stirring at 10°. After 6 hours 50 ml of methanol are added, followed by 200 ml of water. The organic layer is separated, dried and evaporated, to yield the 1,4-benzodioxan-2-yl-acetaldehyde.

Workup

  1. customThe starting material is prepared
  2. customThe organic layer is separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-df082b20fce7436bb80a6d31c41e3b5c
Source dataset
uspto-grants-1979_02
Patent number
US04140781

Reaction notes

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