Water → HCID 23044250, compound

HRID 1248362Notes

Reaction equation

HRID 1248362 reaction equation
C[O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>CCOCC>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[C:8]=2[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydride2×HCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

Product 1

HCID 23044250HCID 23044250, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Over a period of 30 minutes, while stirring, a solution of 1.92 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester in 30 ml of ether is added dropwise to a suspension of 0.21 g of lithium aluminium hydride in 30 ml of ether. The whole is stirred for 1 hour, a further 1.0 g of lithium aluminium hydride is added and stirring is carried out for a further 2 hours. 5 ml of water and, after a short time, 12.5 ml of 2N sulphuric acid are added dropwise thereto, stirring is carried out for 30 minutes and the ether phase is separated off, shaken twice with ether, dried over magnesium sulphate and concentrated to dryness by evaporation. 5-methoxybenzocyclobutene-1-methanol is obtained in the form of a colourless oil.

Workup

  1. stirringThe whole is stirred for 1 hour
  2. stirringstirring
  3. waitis carried out for a further 2 hours
  4. stirringstirring
  5. waitis carried out for 30 minutes
  6. customthe ether phase is separated off
  7. stirringshaken twice with ether
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-b5b3a7087f2c412ba4adfabb345bcc20
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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