Sulfuric Acid → HCID 23044216, compound

HRID 1762592Notes

Reaction equation

HRID 1762592 reaction equation
[O:1]1[CH2:5]CCC1.[H-].[CH2:7]([Al+]CC(C)C)[CH:8]([CH3:10])C.[Cl-].[NH4+].S(=O)(=O)(O)[OH:19].[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH3:5][O:1][C:25]1[CH:24]=[CH:23][C:28]2[CH:10]=[C:8]([CH:7]=[O:19])[C:27]=2[CH:26]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 23044216HCID 23044216, compound

Procedure

10 g (63 mmol) of 5-methoxybenzocyclobutene-1-carboxylic acid nitrile are introduced at -60° C. under argon into 200 ml of tetrahydrofuran. While stirring, 15 ml (75 mmol) of a 1 molar solution of diisobutylaluminium hydride in hexane are slowly added dropwise The reaction mixture is then allowed to warm slowly to room temperature and is stirred for a further 4 hours. At room temperature, 500 ml of saturated ammonium chloride solution are then added and the whole is subsequently stirred for 40 minutes. 220 ml of 5% sulphuric acid are added and extraction is carried out twice with diethyl ether. The combined organic phases are dried and concentrated. The crude product is purified by chromatography on the ten-fold amount of silica gel. 5-methoxybenzocyclobutene-1-carboxaldehyde, Rf=0.23, hexane/ethyl acetate (9:1), is obtained.

Workup

  1. stirringis stirred for a further 4 hours
  2. stirringthe whole is subsequently stirred for 40 minutes
  3. extractionextraction
  4. customThe combined organic phases are dried
  5. concentrationconcentrated
  6. customThe crude product is purified by chromatography on the ten-fold amount of silica gel

Sources & evidence

ORD record
ord-96457ec66dfa427495b45b3d8f036206
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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