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Hydrochloric Acid → (2R, 4 R)-2-{(4-octyloxybenzoyloxy)phenyl)-4-decanolide

HRID 346086
Notes
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Reaction equation

HRID 346086 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][C@@H:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:11][C:9]2=[O:10])=[CH:4][CH:3]=1.[CH2:20]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].N1C=CC=CC=1.Cl.CC[O:47]CC>ClCCl>[CH2:20]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:47][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[C@H:8]2[CH2:13][C@@H:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:11][C:9]2=[O:10])=[O:34])=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 3283Diethyl EtherHCID 27602504-Octyloxybenzoyl chlorideHCID 15653390(2R,4R)-2-(4-hydroxyphenyl)-4-decanolide

Product 1

HCID 131717046(2R, 4 R)-2-{(4-octyloxybenzoyloxy)phenyl)-4-decanolide
Yield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 4 ml of dichloromethane were dissolved 50 mg of (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide obtained in Example 3 and 49 mg of 4-octyloxybenzoyl chloride. To this solution was added 1 ml of pyridine. The resulting mixture was stirred for 6 hours under heating to reflux. The reaction mixture was allowed to cool, and then 50 ml of ether and diluted hydrochloric acid were added thereto. The resulting organic layer was separated, washed with water, and then dried with anhydrous sodium sulfate. The solvent was removed by evaporation and the resulting crude produce was purified by silica gel column chromatography, thereby obtaining 65 mg of crystals of the desired compound (yield 70%).

Workup

  1. temperatureunder heating to reflux
  2. temperatureto cool
  3. customThe resulting organic layer was separated
  4. washwashed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe resulting crude produce
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b894cfc4840f4b88a6acd51b9015b5da
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05061398

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes