Chloroacetyl chloride → HCID 88454521, compound

HRID 484546Notes

Reaction equation

HRID 484546 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][CH2:23][C:24](Cl)=[O:25].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCCCCC>[Cl:22][CH2:23][C:24]([O:21][C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C@H:15]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:25]

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18653088HCID 18653088, compound

Product 1

HCID 88454521HCID 88454521, compoundYield 109%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

In a 1 L round bottom flask equipped with a magnetic stirrer, thermometer and condenser is placed 65 g (0.23 mol) of trans-2-(2'-benzyloxyphenyl)cyclohexanol. This is dissolved in 200 ml of methylenechloride, and then 28.5 g (0.25 mol) of chloroacetyl chloride is added followed by 0.14 g (0.001 mol) of 4-dimethylaminopyridine. The mixture is heated to reflux and monitored by TLC (silica gel: 20% ethyl acetate, hexane). After 4 hours TLC shows the reaction to be complete, it is cooled to room temperature and 200 ml of saturated sodium bicarbonate is added. The reaction mixture is stirred rapidly for another 3 hours. The organic phase is then separated, dried with anhydrous potassium carbonate, filtered and evaporated under reduced pressure to yield 90 g of an amber oil. This oil is dissolved in 100 ml of hexane from which it crystallizes to afford 74 g of off-white solid trans-2-(2'-benzyloxyphenyl)cyclohexyl chloroacetate, which is used directly in the next step.

Workup

  1. customIn a 1 L round bottom flask equipped with a magnetic stirrer
  2. customthermometer and condenser is placed
  3. temperatureThe mixture is heated
  4. temperatureto reflux
  5. customthe reaction
  6. customThe organic phase is then separated
  7. dry with materialdried with anhydrous potassium carbonate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b0cfbaf2c9444ca0a678c29f2f350698
Source dataset
uspto-grants-1993_07
Patent number
US05231198

Reaction notes

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