Ethyl Acetate → 3-Benzyloxy-5-chlorobenzyl alcohol

HRID 2306177Notes

Reaction equation

HRID 2306177 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.[OH-].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 108799093-(Benzoxy)-5-chlorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 110861343-Benzyloxy-5-chlorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-benzyloxy-5-chlorobenzoic acid, as described above in Step B, (5.0 g, 19 mmol) in dry THF (150 mL) at 0° C., under argon, was added LiAlH4 (29 mL of a 1.0 M solution in THF, 29 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 3 hours, then EtOAc (1 mL) was added, followed by water (1 mL), then 15% aqueous NaOH (1 mL), then water (3 mL). The resulting mixture was filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica, eluting with hexane—20% EtOAc to yield the desired product as a colorless oil.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by flash column chromatography on silica
  4. washeluting with hexane—20% EtOAc

Sources & evidence

ORD record
ord-11ef5e2887164aa2a9bf698803f9befa
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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