Hydrochloric Acid → HCID 10905876, compound

HRID 567162Notes

Reaction equation

HRID 567162 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:30]=[CH:29][C:15]([C:16]([CH:18]([OH:28])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:17])=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>O1CCCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([CH:18]([O:28][C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:17])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 18376478HCID 18376478, compound

Product 1

HCID 10905876HCID 10905876, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl chloroformate (14.1 g) was added dropwise to a mixture of ethyl 6-(4-chlorobenzoyl)-6-hydroxyhexanoate (24.5 g), pyridine(7.14 g) and tetrahydrofuran(200 ml) with cooling with ice. After stirring for 3 hours at room temperature, the reaction mixture was poured into ice water, and neutrized by 2N-hydrochloric acid. This was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The solvent was evaporated to give ethyl 6-(4-chlorobenzoyl)-6-phenoxycarbonyloxyhexanate(32.3 g, 94%) as an oily substance.

Workup

  1. temperaturewith cooling with ice
  2. extractionThis was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-34517acd016341cbaf3afd441a1774a5
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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