Water → (3-Methoxy-1,2-phenylene)dimethanol

HRID 2417563Notes

Reaction equation

HRID 2417563 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:5]([C:6](O)=[O:7])[C:4]=1[C:12](O)=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:5]([CH2:6][OH:7])[C:4]=1[CH2:12][OH:13]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3152183-Methoxyphthalic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 14892485(3-Methoxy-1,2-phenylene)dimethanolYield 71.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-methoxyphthalic acid (19.6 g, 0.1 mol) in 100 ml of tetrahydrofuran was added to 10 g (0.263 mol) of lithium aluminum hydride in 500 ml of anhydrous ether at a rate sufficient to maintain a constant reflux. The mixture was refluxed for 2 hours after the addition was completed. It was cooled and decomposed by the addition of 10 ml of water, 20 ml of 10% sodium hydroxide and 40 ml of water. The resulting solid was separated by filtration and washed with tetrahydrofuran. The combined filtrates were concentrated to give 12 g of 3-methoxy-o-xylene-α,α'-diol; m.p. 95°.

Workup

  1. temperatureto maintain a constant reflux
  2. temperatureThe mixture was refluxed for 2 hours
  3. additionafter the addition
  4. temperatureIt was cooled
  5. customThe resulting solid was separated by filtration
  6. washwashed with tetrahydrofuran
  7. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-c33fca0e0705493fbfb989728a2ded73
Source dataset
uspto-grants-1984_09
Patent number
US04469634

Reaction notes

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