Dimethyl Sulfide → 2-Phenoxybenzyl alcohol

HRID 2248018Notes

Reaction equation

HRID 2248018 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CSC>C1COCC1>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 6331BoraneHCID 752372-Phenoxybenzoic acid

Product 1

HCID 36601112-Phenoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenoxybenzoic acid (10.00 g, 46.7 mmol) in THF (250 mL) was added dropwise borane.dimethylsulfide (9.8 mL of a 10.0 M solution, 98 mmol). Upon completion of addition, the reaction was stirred for 15 hrs. It was then quenched with aqueous 10% HCl (250 mL) and extracted with ethylacetate (3×250 mL). The organics were combined, dried with MgSO4 and concentrated to afford crude 2-phenoxybenzyl alcohol.

Workup

  1. additionUpon completion of addition
  2. customIt was then quenched with aqueous 10% HCl (250 mL)
  3. extractionextracted with ethylacetate (3×250 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b7094abaa26f4459a41359a5afd3a37a
Source dataset
uspto-grants-1991_08
Patent number
US05037853

Reaction notes

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