Water → (4-Methoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanol

HRID 1905737Notes

Reaction equation

HRID 1905737 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([C:10](O)=[O:11])[C:7]=2[CH:13]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>CCOCC>[CH3:1][O:2][C:3]1[CH:13]=[C:7]2[CH:8]([CH2:10][OH:11])[CH2:9][C:6]2=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178487220HCID 178487220, compound

Product 1

HCID 13247995(4-Methoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5-methoxybenzocyclobutene-1-carboxylic acid (32.0 g) in ether (1.2 l) is added dropwise to a stirred suspension of LAH (15.5 g) in ether (650 ml) under nitrogen. The reaction mixture is stirred at RT for 4 hours, after which, water (15.5 ml), 15% NaOH (15.5 ml) and a second portion of water added (46 ml) sequentially to the reaction mixture resulting in the formation of a precipitate. The ethereal layer is filtered, dried over Na2SO4, filtered and concentrated in vacuo yielding the desired product as an oil.

Workup

  1. customresulting in the formation of a precipitate
  2. filtrationThe ethereal layer is filtered
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c203e6669eef4721a7a62e341f58b40a
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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