Acetyl chloride → HCID 22416519, compound

HRID 1720868Notes

Reaction equation

HRID 1720868 reaction equation
[CH2:1]([C:3]1(O)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)[CH3:2].C(Cl)(=O)C>C(O)(=O)C>[CH:1](=[C:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 15818605HCID 15818605, compound

Product 1

HCID 22416519HCID 22416519, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

8.5 g of 5-ethyl-5H-dibenzo[a,d]cycloheptene-5-ol are dissolved in 70 ml of glacial acetic acid and 14 ml of acetyl chloride and the mixture is stirred and warmed at 95° C. overnight. Evaporation to dryness leads to a red oily residue which is dissolved in ethyl acetate, washed with water and dried on sodium sulfate. Evaporation affords 8.26 g of a crude oil which is purified by flash chromatography (cyclohexane) yielding 8.27 g (78%) of the pure title compound. A 96.5% yield can be obtained with a 3 days reaction time.

Workup

  1. customEvaporation to dryness
  2. dissolutionis dissolved in ethyl acetate
  3. washwashed with water
  4. customdried on sodium sulfate
  5. customEvaporation
  6. customaffords 8.26 g of a crude oil which
  7. customis purified by flash chromatography (cyclohexane)

Sources & evidence

ORD record
ord-5b3985c39e3d49cd86459dd97160bd46
Source dataset
uspto-grants-1996_04
Patent number
US05508280

Reaction notes

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