Acetyl chloride → 1-Chloro-4-(chloro-prop-2-ynyloxy-methyl)-benzene

HRID 1092903Notes

Reaction equation

[CH2:1]([O:4][CH:5](OCC#C)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[C:2]#[CH:3].C([Cl:20])(=O)C.S(Cl)(Cl)=O>>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([Cl:20])[O:4][CH2:1][C:2]#[CH:3])=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 6367Acetyl chloride

HCID 24386Thionyl Chloride

HCID 576886141-(Bis-prop-2-ynyloxy-methyl)-4-chloro-benzene

Product 1

HCID 576886121-Chloro-4-(chloro-prop-2-ynyloxy-methyl)-benzeneYield 125%

Conditions

Temperature: 20 °C

Procedure

1-(Bis-prop-2-ynyloxy-methyl)-4-chloro-benzene (11.7 g) is added to acetyl chloride (19.9 g) and thionyl chloride (0.2 ml) over 1 hour. The temperature is maintained at 20° C. by occasionally cooling. The reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is evaporated at 20-30° C. using vacuum. 1-Chloro-4-(chloro-prop-2-ynyloxy-methyl)-benzene (13.4 g) is obtained as oil.

Workup

temperatureby occasionally cooling
customThe reaction mixture is evaporated at 20-30° C.

Sources & evidence

ORD record: ord-9b184885ce2146a4a6800a9bf56a4d5f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129560B2

Reaction notes

Loading…