Propargyl bromide → 1-(3-Butynyl)-3,6-dimethoxy-2,4,5-trimethylbenzene

HRID 1195467Notes

Reaction equation

HRID 1195467 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH2:11]Cl)=[C:9]([CH3:13])[C:6]([O:7][CH3:8])=[C:5]([CH3:14])[C:4]=1[CH3:15].[Mg].[CH2:17](Br)[C:18]#[CH:19]>C1COCC1.CCOCC.[I-].[Na+]>[CH2:11]([C:10]1[C:3]([O:2][CH3:1])=[C:4]([CH3:15])[C:5]([CH3:14])=[C:6]([O:7][CH3:8])[C:9]=1[CH3:13])[CH2:19][C:18]#[CH:17]

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 5462224MagnesiumHCID 108789291-(Chloromethyl)-2,5-dimethoxy-3,4,6-trimethylbenzene

Product 1

HCID 216084171-(3-Butynyl)-3,6-dimethoxy-2,4,5-trimethylbenzeneYield 96.3%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of chloromethyltrimethylhydroquinone dimethyl ether (7.5 g; 32 mmol) in THF (20 ml) was treated dropwise at 0° with a freshly Prepared solution of a Grignard reagent Prepared from 1.9 g of magnesium shavings and 4.91 ml (65 mmol) of propargyl bromide. After the addition of solid sodium iodide (0.42 g) the mixture was warmed to room temperature and stirred overnight. Thereafter, the reaction mixture was diluted with ether and washed with 2N hydrochloric acid. The ethereal solution was deacidified with bicarbonate, dried and freed from solvent. Distillation (0.04 mbar; 140° C.) of the residue gave 7.16 g of 1-(3-butynyl)-3,6-dimethoxy-2,4,5-trimethylbenzene; melting point: 54° C.

Workup

  1. washwashed with 2N hydrochloric acid
  2. customdried
  3. distillationDistillation (0.04 mbar; 140° C.) of the residue

Sources & evidence

ORD record
ord-a79de7c350f041f6a90a4184f9a6ada7
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

Loading…