Hydrochloric Acid → HCID 20161182, compound

HRID 247018Notes

Reaction equation

HRID 247018 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([C:14]#N)=[CH:6]2.[H-].C([Al+]CC(C)C)C(C)C.C[OH:27].Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([CH:14]=[O:27])=[CH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 20161200HCID 20161200, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20161182HCID 20161182, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-5 °C

Procedure

5,6-Dimethoxy-1H-indene-2-carbonitrile (1.8 g) was suspended in dry toluene (40 ml) under an atmosphere of nitrogen. The reaction mixture was cooled to -5° C. and treated dropwise with a solution of diisobutylaluminium hydride in toluene (1.5M, 13 ml). After 30 minutes the solution was treated with methanol (5 ml) then poured into hydrochloric acid (1M, 200 ml) and stirred for 15 minutes. The resultant solution was extracted into dichloromethane (4×100 ml) then the organic extracts were combined, washed with brine, dried over magnesium sulphate and evaporated to dryness. The residue (1.4 g) was crystallised from dichloromethane:ether to give 5,6-dimethoxy-1-H-indene-2-carboxaldehyde as a white solid, m.p. 125°-128° C.

Workup

  1. extractionThe resultant solution was extracted into dichloromethane (4×100 ml)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue (1.4 g) was crystallised from dichloromethane

Sources & evidence

ORD record
ord-09f438ec31564fc782eae76b2e281f46
Source dataset
uspto-grants-1987_11
Patent number
US04705782

Reaction notes

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