Water → 4-Benzyloxy-3-methylcarbonyl-1-(2,3-epoxypropoxy) Benzene

HRID 480041Notes

Reaction equation

HRID 480041 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:4][C:3]=1[C:13]([CH3:15])=[O:14].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:4][C:3]=1[C:13]([CH3:15])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 57143294HCID 57143294, compound

Product 1

HCID 178870844-Benzyloxy-3-methylcarbonyl-1-(2,3-epoxypropoxy) Benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution containing 1 g (0.0048 mole) of the product of example 39, 0.856 ml (0.00072 mole) of benzyl bromide and 0.924 g (0.0072 mole) of K2CO3 in 12 ml of acetone are heated for 6 hours under reflux in nitrogen. Then 0.5 ml (0.0042 mole) of benzyl bromide are added and the mixture heated for a further 7 hours. The substance is poured into water, extracted with ethyl acetate and the solvent evaporated off . The reaction product is purified by chromatography, eluting with an 8/2 mixture of hexane and acetone. The required product is obtained, MP: 45-48° C.

Workup

  1. temperatureare heated for 6 hours
  2. temperatureunder reflux in nitrogen
  3. temperaturethe mixture heated for a further 7 hours
  4. extractionextracted with ethyl acetate
  5. customthe solvent evaporated off
  6. customThe reaction product is purified by chromatography
  7. washeluting with an 8/2 mixture of hexane and acetone

Sources & evidence

ORD record
ord-f0deee0d8285412697561ff1f9d7edb9
Source dataset
uspto-grants-2003_11
Patent number
US06649627B1

Reaction notes

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