Benzyl Alcohol → HCID 19018237, compound

HRID 1728450Notes

Reaction equation

HRID 1728450 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.CC[O:29]C(C)=O>ClCCl.O>[CH2:12]([C:10]1[CH:11]=[C:3]([CH2:2][Cl:1])[CH:4]=[CH:5][C:6]=1[C:7]([OH:29])=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 19018237HCID 19018237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred suspension of 3.0 g (14 mmol) of 4-(bromomethyl)benzoic acid and 3.5 ml (41 mmol) of oxalyl chloride in 35 ml of dichloromethane was refluxed for 10 hours and cooled to room temperature. Evaporation afforded 4-(chloromethyl)benzoyl chloride as an oil which was used without purification. To a cooled (0° C.) solution of 2.6 g (14 mmol) of 4-(chloromethyl)benzoyl chloride and 2.0 g (18 mmol) of benzyl alcohol in 30 ml of dichloromethane was added 1.8 g (18 mmol) of triethylamine. The reaction was stirred at 0° C. for 0.2 hours, then at room temperature for an additional 1 hour and poured into 150 ml of EtOAc. The EtOAc layer was with three portions of water, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed (5% EtOAc/hexanes) to give 0.7 g of product; m.p. 52°-54° C.

Workup

  1. customwas used without purification
  2. waitat room temperature for an additional 1 hour
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1128eb7441804bfdb2bf67f66940e54b
Source dataset
uspto-grants-1994_07
Patent number
US05326905

Reaction notes

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