Hydrochloric Acid → HCID 54260772, compound

HRID 2396121Notes

Reaction equation

HRID 2396121 reaction equation
Cl[CH:2]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][CH:24]([OH:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].Cl>C1C=CC=CC=1.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH2:25]([CH:24]([O:32][CH:2]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:23][CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11117878Acetic acid, chloro(phenylthio)-, ethyl esterHCID 53868356HCID 53868356, compound

Product 1

HCID 54260772HCID 54260772, compound

Reagents, catalysts & solvents 2

HCID 2724192Zinc acetate (USP)CatalystHCID 241BenzeneSolvent

Procedure

Part B. The method of Speckamp et al., Tetrahedron Letters, v. 32, p. 1491 (1991), is employed here. Thus, a solution of ethyl 2-chloro-2-(phenylthio)acetate [prepared according to the method of Bohme et al., Liebigs Annalen der Chemie, p. 51 (1977)], 7-heptadecen-10-ol, andcatalytic zinc acetate dihydrate in benzene is heated to reflux under a Dean-Stark trap until the formation of hydrogen chloride is complete. Workup according to the listed reference affords ethyl 2-(1-heptyl-3-decen-1-oxy)-2-(phenylthio)acetate.

Sources & evidence

ORD record
ord-78ae3be7a50b40869bcd31437823f248
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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