Allyl chloride → HCID 10933990, compound

HRID 1578544Notes

Reaction equation

HRID 1578544 reaction equation
[OH-].[Na+].[C:3]1([C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:19](Cl)[CH:20]=[CH2:21]>CS(C)=O>[CH2:21]([C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([OH:12])[C:9](=[O:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 8400BenzoinHCID 14798Sodium Hydroxide

Product 1

HCID 10933990HCID 10933990, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

90 ml of a 10% by weight aqueous sodium hydroxide solution are added with cooling in a nitrogen atmosphere to a solution of 42.4 g (0.2 mol) benzoin in 400 ml DMSO, and 22 ml (0.27 mol) allyl chloride are added dropwise at 20°C within 15 minutes. The reaction solution is further stirred for 2 hours and then poured into ice/water. The crystalline crude product (50 g) is recrystallised from petroleum ether and gives 37.9 g (75% of theory) α-allyl-benzoin of melting point 89°- 93°C. A further 5.1 g of melting point 85°- 90°C are obtained from the mother liquor.

Workup

  1. additionare added dropwise at 20°C within 15 minutes
  2. customThe crystalline crude product (50 g) is recrystallised from petroleum ether

Sources & evidence

ORD record
ord-9aab255b049d49de8d644297dfa1500f
Source dataset
uspto-grants-1976_02
Patent number
US03937722

Reaction notes

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