Tetrahydrofuran → (4-Methoxy-1,2-phenylene)dimethanol

HRID 1041233Notes

Reaction equation

HRID 1041233 reaction equation
[AlH4-].[Li+].O1CCCC1.C[O:9][C:10](=O)[C:11]1[C:12](=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:13](OC)=[O:14]>>[OH:14][CH2:13][C:12]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:11]=1[CH2:10][OH:9]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 28112Lithium aluminum hydrideHCID 736307Dimethyl 4-methoxyphthalate

Product 1

HCID 12577527(4-Methoxy-1,2-phenylene)dimethanolYield 97%

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of Lithium tetrahydroaluminate (16.6 g, 0.436 mol) in Tetrahydrofuran (300 mL, 4 mol) at 0° C. under nitrogen was added dropwise a solution of 4-Methoxy-phthalic acid dimethyl ester (24.46 g, 0.1091 mol) in Tetrahydrofuran (100 mL, 1 mol). The reaction was stirred at 0° C. for 1 h then warmed to room temperature overnight. HPLC indicated no starting material present. Reaction was recooled at 0° C. and quenched with addition of water (125 mL) carefully dropwise, 1 N NaOH (100 mL) and water (125 mL). Evolution of gas was observed upon initial quenching with water. A white solid precipitated out of solution (aluminum salts). Following complete quenching of the reaction mixture, the aluminum salts were removed by filtration. The filtrate was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 17.80 grams (97%) of (2-Hydroxymethyl-4-methoxy-phenyl)-methanol as a colorless oil.

Workup

  1. temperaturethen warmed to room temperature overnight
  2. customReaction
  3. customwas recooled at 0° C.
  4. customquenched with addition of water (125 mL) carefully dropwise
  5. customupon initial quenching with water
  6. customA white solid precipitated out of solution (aluminum salts)
  7. customFollowing complete quenching of the reaction mixture
  8. customthe aluminum salts were removed by filtration
  9. additionThe filtrate was diluted with ethyl acetate
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c1e27afd2294d91ad06c1e25310cd46
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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