Hydrochloric Acid → 9-Anthracenemethanol, acetate

HRID 1939129Notes

Reaction equation

HRID 1939129 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25].Cl>C(Cl)Cl.O1CCOCC1>[C:24]([O:16][CH2:15][C:13]1[C:12]2[C:7]([CH:6]=[C:5]3[C:14]=1[CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 738489-Anthracenemethanol

Product 1

HCID 278769-Anthracenemethanol, acetateYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 9-anthracenemethanol (15.0 g, 72 mmole) and triethylamine (7.3 g, 72 mmole) in methylene chloride (100 ml) and 1,4-dioxane (120 ml) was cooled. Acetyl chloride (6.8 g, 86.4 mmole) was added dropwise to the solution at 5°-10° C. and reacted with stirring for 2.5 hours at same temperature. After reaction, the reaction mixture was poured into ice-cold H2O (350 ml), acidified with 10% aqueous HCl, extracted with methylene chloride (100 ml). The resulting organic layer was washed with H2O (100 ml×1), saturated aqueous sodium bicarbonate (100 ml×1) and H2O (100 ml×1), dried over anhydrous MgSO4 and evaporated. The residual crude solid (17.7 g) was recrystallized from n-hexane to give 11.0 g of 9-anthrylmethyl acetate as yellow needles having a melting point of 110.0°-111.5° C.

Workup

  1. customreacted
  2. customAfter reaction
  3. extractionextracted with methylene chloride (100 ml)
  4. washThe resulting organic layer was washed with H2O (100 ml×1), saturated aqueous sodium bicarbonate (100 ml×1) and H2O (100 ml×1)
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. customThe residual crude solid (17.7 g) was recrystallized from n-hexane

Sources & evidence

ORD record
ord-db8068bafe49424da63dea221a90318d
Source dataset
uspto-grants-1997_12
Patent number
US05695910

Reaction notes

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