Hydrogen Peroxide → HCID 18787388, compound

HRID 1602432Notes

Reaction equation

HRID 1602432 reaction equation
[CH2:1]([C:4]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:2]=[CH2:3].[OH:23]O>C1COCC1.C([O-])(O)=O.[Na+]>[OH:23][CH2:3][CH2:2][CH2:1][C:4]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 18522258HCID 18522258, compound

Product 1

HCID 18787388HCID 18787388, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of ethyl 2-allyl-3-benzyloxybenzoate (29.6 g, 100 mmol) in THF (300 ml) was cooled to -10° C. under nitrogen. A solution of borane THF complex (110 ml of 1M, 110 mmol) was added dropwise, and the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. A solution of hydrogen peroxide (12 ml) in saturated NaHCO3 (200 ml) was then slowly added, and the mixture was stirred for 30 min. The mixture was extracted with ethyl acetate twice. The ethyl acetate extracts were washed with water, dried over brine, and then concentrated in vacuo to give a clear oil (27.6 g, 88%).

Workup

  1. additionA solution of borane THF complex (110 ml of 1M, 110 mmol) was added dropwise
  2. stirringthe mixture was stirred for 30 min
  3. extractionThe mixture was extracted with ethyl acetate twice
  4. washThe ethyl acetate extracts were washed with water
  5. dry with materialdried over brine
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3f62ea8b79f418aac37620eee60c159
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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