Dimethyl Sulfide → HCID 69964102, compound

HRID 1458299Notes

Reaction equation

HRID 1458299 reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[CH2:12]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]O)=[CH:25][CH:24]=1)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15]>ClCCl.[Cl-].[Na+].O>[CH2:12]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][Cl:1])=[CH:25][CH:24]=1)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 69963640HCID 69963640, compound

Product 1

HCID 69964102HCID 69964102, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of N-chorosuccinimide (1.15 g) in dichloromethane (40 ml) was added dimethylsulfide (0.72 g) while being cooled with ice. Then, a solution of 4-geranyloxybenzyl alcohol (1.50 g) in dichloromethane (10 ml) was added thereto and the resulting mixture was stirred for 3 hours at room temperature. The reaction solution, with brine added thereto, was extracted with ethyl acetate. The extract was concentrated under a vacuum to yield a raw product of 4-geranyloxybenzyl chloride.

Workup

  1. temperaturewhile being cooled with ice
  2. extractionwas extracted with ethyl acetate
  3. concentrationThe extract was concentrated under a vacuum

Sources & evidence

ORD record
ord-ffd3970018404c5dabbb46d60b112661
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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