Tetrahydrofuran → 4-(4-Hydroxymethylphenyl)phenol

HRID 1873384Notes

Reaction equation

HRID 1873384 reaction equation
O[C:2]1([C:14]([O:16]CC)=O)[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C.C1C[O:32]CC1>C1(C)C=CC=CC=1>[OH:16][CH2:14][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:32])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 68717694HCID 68717694, compound

Product 1

HCID 220621304-(4-Hydroxymethylphenyl)phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15.0 g (60.7 mmol) of ethyl 4-hydroxybiphenyl-4-carboxylate are dissolved in 500 ml of THF, and 200 ml of a 1 M solution of diisobutylaluminium hydride in toluene are added at −70° C. The cooling is subsequently removed, and the batch is stirred at room temp. for 2 h. After addition of 5 ml of isopropanol, the solution is added to water, extracted three times with MTB ether, and the combined org. phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with toluene/ethyl acetate, giving 4′-hydroxymethyl-4-biphenylol as a colourless solid.

Workup

  1. customThe cooling is subsequently removed
  2. additionAfter addition of 5 ml of isopropanol
  3. additionthe solution is added to water
  4. extractionextracted three times with MTB ether
  5. washphases are washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. filtrationthe residue is filtered through silica gel with toluene/ethyl acetate

Sources & evidence

ORD record
ord-c3be5cd1652a46af897cbea91c6adc5f
Source dataset
uspto-grants-2012_11
Patent number
US08304035B2

Reaction notes

Loading…