Water → HCID 14989171, compound

HRID 981602Notes

Reaction equation

HRID 981602 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[CH:21]1(CO)C[CH2:22]1>C[O-].[Na+].C1C=CC=CC=1>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21]3)=[O:14])=[CH:18][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 75644CyclopropanemethanolHCID 191414Ethyl 4-(phenylmethoxy)benzoate

Product 1

HCID 14989171HCID 14989171, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 241BenzeneSolvent2×

Procedure

A mixture of 12.8 parts of ethyl 4-(phenylmethoxy)benzoate, 180 parts of benzene and 5 drops of a sodium methoxide solution 30% was stirred and refluxed using a water separator. 10.8 Parts of cyclopropanemethanol in 90 parts of benzene was added dropwise during a period of 1 hour. Upon complete addition, stirring was continued for 4 hours at reflux. After cooling, the whole was washed with water, the organic layer was dried, filtered and evaporated, yielding 14 parts (100%) of (cyclopropylmethyl) 4-(phenylmethoxy)benzoate as a residue (int. 3).

Workup

  1. temperaturerefluxed
  2. additionUpon complete addition
  3. stirringstirring
  4. temperatureat reflux
  5. temperatureAfter cooling
  6. washthe whole was washed with water
  7. customthe organic layer was dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6201f9f5cbac4b709365a877eacdd981
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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