Hydrochloric Acid → 3-(3,4-Dichlorophenyl)-2-propene-1-ol acetate

HRID 481432

Reaction equation

HRID 481432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.[CH3:19][C:20](Cl)=[O:21].Cl>ClCl.CN(C1C=CC=CN=1)C>[C:20]([O:12][CH2:11][CH:10]=[CH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:21])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 537091912-Propen-1-ol, 3-(3,4-dichlorophenyl)-

Product 1

HCID 538528443-(3,4-Dichlorophenyl)-2-propene-1-ol acetateYield 97%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 24526ChlorineSolvent

Conditions

Temperature
23 °C

Procedure

Treat a solution of the product of step 2 (13.2 g, 65 mmol) in CH2 Cl2 (250 mL) at 0° C. with pyridine (7.89 mL, 97.5 mmol, 1.5 eq) and dimethylaminopyridine (397 mg, 3.25 0.05 eq), followed by CH3COCl (6.48 mL, 74.75 mmol, 1.15 eq). Allow the mixture to warm to 23° C., pour into 1M HCl (100 mL) and wash the resulting organic layer again with 1M HCl (100 mL), followed by water (5×100 mL; pH=6.5-7). Dry the organic layer (Na2SO4) and concentrate to obtain 15.4 g (62.9 mmol, 97%) of 3-(3,4-dichlorophenyl)-2-propene-1-ol acetate as a colorless oil.

Workup

  1. washwash the resulting organic layer again with 1M HCl (100 mL)
  2. dry with materialDry the organic layer (Na2SO4)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-c6b90149cc644b18a385fbb3bcd67adf
Source dataset
uspto-grants-1998_08
Patent number
US05789422

Linked notes

Loading…