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Hydrochloric Acid → 4-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl sulfoxide

HRID 6517
Notes
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Reaction equation

HRID 6517 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]1([CH3:31])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=3)[CH:11]=[CH:10][C:9]1=2.Cl>O.C(O)C.CN(C)C=O>[CH3:7][C:8]1([CH3:31])[CH2:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]2[CH:13]=[C:12]([S:20]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=3)=[O:2])[CH:11]=[CH:10][C:9]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 148505884-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl thioetherHCID 23667635Sodium periodate

Product 1

HCID 148505894-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl sulfoxideYield 39.6%

Reagents, catalysts & solvents 3

HCID 702Ethanol
Solvent
HCID 962WaterSolvent2×
HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.4 g (16 mmol) of sodium periodate in 30 ml of water was added dropwise to 5.3 g (15 mmol) of the thioether from Example 10 in a mixture of 150 ml of ethanol and 40 ml of dimethylformamide at 0° C., and the mixture was then stirred at the same temperature for 2 hours and at room temperature overnight. The reaction solution was then poured into water, the pH was adjusted to 5 with 2N hydrochloric acid, the mixture was extracted with dichloromethane, and the organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure. Crystallization of the oily residue from ethanol yielded 2.2 g of title compound of melting point 198°-200° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washthe organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customCrystallization of the oily residue from ethanol

Sources & evidence

ORD record
ord-3975e3cba1d24b4fba5c7e42d9b53709
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05248823

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes