Diethyl Ether → 1-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanone

HRID 1910592Notes

Reaction equation

HRID 1910592 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([OH:14])[CH3:13])[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C(OCC)C>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 587072601-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 587072841-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanol (258 mg, 1.20 mmol) was dissolved in 4 mL of dichloromethane. PCC (648 mg, 3.00 mmol) was added portionwise and the mixture was stirred for 16 h (reaction is likely to be completed earlier). Diethyl ether (20 mL) was added and stirred for 10 minutes. The heterogeneous mixture was filtered through a plug of celite. The solvent was removed by rotary evaporation to collect the desired product (248 mg, 97%). 1H NMR (400 MHz, CDCl3): δ 7.28 (d, 1H), 7.01 (d, 1H), 4.33 (m, 4H), 2.59 (s, 3H).

Workup

  1. customreaction
  2. stirringstirred for 10 minutes
  3. filtrationThe heterogeneous mixture was filtered through a plug of celite
  4. customThe solvent was removed by rotary evaporation
  5. customto collect the desired product (248 mg, 97%)

Sources & evidence

ORD record
ord-0cadcb9d4fd94dde95eb37519b13910d
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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