Hydrochloric Acid → Acetoxy-1-(3-chlorophenyl)-2-(2-tertbutoxyethoxy)ethane

HRID 2259347Notes

Reaction equation

HRID 2259347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:18])[CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].Cl>C(Cl)Cl>[C:25]([O:18][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]([CH3:15])([CH3:17])[CH3:16])(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 538355021-(3-Chlorophenyl)-2-(2-tertbutoxyethoxy)ethanol

Product 1

HCID 53824717Acetoxy-1-(3-chlorophenyl)-2-(2-tertbutoxyethoxy)ethaneYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

37.0 g of 1-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethanol was dissolved in 70 ml of methylene chloride. To the solution were added 12.9 g of pyridine and 16.6 g of acetic anhydride. The resulting mixture was stirred for 24 hours at room temperature. The reaction mixture was added to a mixture of 150 ml of ice water and 100 ml of methylene chloride. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with a saturatred aqueous sodium hydrogencarbonate solution and water in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 40.0 g of oily 1-acetoxy-1-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethane.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturatred aqueous sodium hydrogencarbonate solution and water in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f6387223d94e4d08a46eaaca6fb12784
Source dataset
uspto-grants-1995_12
Patent number
US05472984

Reaction notes

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