Methyl 3-(4-hydroxyphenyl)benzoate → 4-(3-Hydroxymethylphenyl)phenol

HRID 1600945Notes

Reaction equation

HRID 1600945 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=O>O1CCCC1>[OH:8][CH2:9][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 5097337Methyl 3-(4-hydroxyphenyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 218306904-(3-Hydroxymethylphenyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminium hydride (1 M in ether, 2.5 ml) was added to dry tetrahydrofuran (10 ml) and the solution cooled to 0° C. A solution of 3'-methoxycarbonylbiphenyl-4-ol in (0.57 g) in tetrahydrofuran (10 ml) was then added and the resulting solution stirred at room temperature for 30 minutes. The reaction was then quenched by the addition of water (0.1 ml) followed by aqueous sodium hydroxide (50%, 0.1 ml) and then water (0.5 ml). The mixture was acidified with dilute aqueous hydrochloric acid (2 M) and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the sub-title compound as a white solid (0.48 g).

Workup

  1. customThe reaction was then quenched by the addition of water (0.1 ml)
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b184d30990c42269ec39029db9c71cc
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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