Benzyl Alcohol → [3-(Benzyloxy)-4-methylphenyl]methanol

HRID 73326Notes

Reaction equation

HRID 73326 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]=1)C1C=CC=CC=1.O.C(O)C1C=CC=CC=1>C(OCC)C>[CH2:24]([O:23][C:18]1[CH:17]=[C:16]([CH2:15][OH:14])[CH:21]=[CH:20][C:19]=1[CH3:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 584372413-Benzyloxy-4-methylbenzoic acid benzyl ester

Product 1

HCID 24721056[3-(Benzyloxy)-4-methylphenyl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride in diethyl ether (50 mL) was added dropwise a solution of 3-Benzyloxy-4-methyl-benzoic acid benzyl ester (7.5 g) in diethyl ether (11 mL) under argon atmosphere at 0° C., and this mixture was stirred at room temperature for 6 hours. To this reaction mixture was added dropwise water (3.2 mL), and then Celite was added to this mixture and filtered. This filtrate was concentrated to give title compounds as a mixture of benzyl alcohol (7.0 g).

Workup

  1. additionCelite was added to this mixture
  2. filtrationfiltered
  3. concentrationThis filtrate was concentrated
  4. customto give title compounds

Sources & evidence

ORD record
ord-ea544e622cf2403a8129c2761adca09c
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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