Water → HCID 58935104, compound

HRID 970255Notes

Reaction equation

HRID 970255 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:26])=O.O>ClCCl>[Cl:26][CH2:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 58935107HCID 58935107, compound

Product 1

HCID 58935104HCID 58935104, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.7 g (5.5 mmole) of (E)-4-hydroxymethyl-4′-hexyloxystilbene (21) in 12 ml of dichloromethane cooled in an ice bath under a nitrogen atmosphere were added dropwise 0.5 ml of thionylchloride in 3 ml of dichloromethane. After 1.5 h 16 ml of water were added and the organic layer was separated. It was washed with 12 ml of brine, dried over MgSO4, and the solvent was evaporated. A white solid was obtained which was recrystallized from 80 ml of a 1:1 mixture of hexane and ethanol. 1.1 g of white crystals were obtained (yield 60%).

Workup

  1. customthe organic layer was separated
  2. washIt was washed with 12 ml of brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated
  5. customA white solid was obtained which
  6. customwas recrystallized from 80 ml of a 1:1 mixture of hexane and ethanol

Sources & evidence

ORD record
ord-9376a8cc53264dad87b51e5a480907b2
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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