Phenol → HCID 576791, compound

HRID 1975828Notes

Reaction equation

HRID 1975828 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7](Cl)=[O:8])[CH:2]=1.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]1([O:17][C:7](=[O:8])[C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 743753-Methylbenzoyl chloride

Product 1

HCID 576791HCID 576791, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 23.19 g (0.15 mol) of m-toluoyl chloride in 70 mL of methylene chloride was added dropwise to a solution containing 14.12 g (0.15 mol) of phenol and 16.7 g (0.165 mol) of triethylamine in 70 mL of methylene chloride at ice bath temperature. A precipitate formed upon addition. The reaction mixture was stirred overnight at room temperature and was then filtered. The filtrate was washed successively by water (100 mL) and then by brine (75 mL) The organic layer was removed and dried over magnesium sulfate, filtered and evaporated in a rotary evaporator. The clear liquid product amounted to 29.91 g.

Workup

  1. customA precipitate formed upon addition
  2. filtrationwas then filtered
  3. washThe filtrate was washed successively by water (100 mL)
  4. customby brine (75 mL) The organic layer was removed
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-fadc28cfb16041a5b9fd6be5f18f585b
Source dataset
uspto-grants-1994_02
Patent number
US05288871

Reaction notes

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