2-Chloroethyl methyl sulfide → methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]phenoxy]ethyl sulphide

HRID 1655400Notes

Reaction equation

HRID 1655400 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:23])=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[CH3:25][S:26][CH2:27][CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:23])=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:28][CH2:27][S:26][CH3:25])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 6439236Ro 14-6113

Product 1

HCID 67786645methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]phenoxy]ethyl sulphideYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 g of p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenol, 4.8 g of 2-chloroethyl methyl sulphide and 10.5 g finely powdered potassium carbonate in 100 ml of dimethylformamide is heated to 100° for 20 hours. The cooled reaction mixture is diluted with water and extracted several times with ethyl acetate. The crystalline residue obtained after drying and evaporating the organic phase is recrystallized from hexane and gives 5.5 g of methyl 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenoxy]ethyl sulphide in colourless crystals, melting point 94°-96°.

Workup

  1. temperatureis heated to 100° for 20 hours
  2. customThe cooled reaction mixture
  3. extractionextracted several times with ethyl acetate
  4. customThe crystalline residue obtained
  5. customafter drying
  6. customevaporating the organic phase
  7. customis recrystallized from hexane

Sources & evidence

ORD record
ord-8ef21f0473ed402abd8432a0351fa66f
Source dataset
uspto-grants-1993_10
Patent number
US05250562

Reaction notes

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