Water → HCID 12398564, compound

HRID 866376Notes

Reaction equation

HRID 866376 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>N1C=CC=CC=1>[CH:1]1([O:6][C:19]([C:18]2[CH:22]=[CH:23][C:15]([O:14][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:16][CH:17]=2)=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 7298CyclopentanolHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 12398564HCID 12398564, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopentanol (2.58g.; 0.03 m) was dissolved in pyridine (50 ml), 4-benzyloxybenzoyl chloride (6.76g; 0.03 m) was added and the mixture was boiled under reflux 6 hours. The resulting mixture was added to iced-water, extracted with ether, the organic extract washed with 2×100 ml. of 2N hydrochloric acid, 2×100 ml. saturated sodium bicarbonate solution and 1×100 ml. of water, dried (MgSO4) and evaporated. The ester was purified by elution from a column of silica in toluene.

Workup

  1. temperatureunder reflux 6 hours
  2. extractionextracted with ether
  3. extractionthe organic extract
  4. washwashed with 2×100 ml
  5. dry with materialof water, dried (MgSO4)
  6. customevaporated
  7. customThe ester was purified by elution from a column of silica in toluene

Sources & evidence

ORD record
ord-bf7f3de45ca741678f61c2a1ae740b76
Source dataset
uspto-grants-1978_07
Patent number
US04098816

Reaction notes

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