Hydrochloric Acid → 4-Chloromethyl-2-methoxy-1-pent-2-ynyloxy-benzene

HRID 458245Notes

Reaction equation

HRID 458245 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:15]O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14].[ClH:17]>O1CCOCC1>[Cl:17][CH2:15][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18442092(3-Methoxy-4-pent-2-ynyloxy-phenyl)-methanol

Product 1

HCID 184420934-Chloromethyl-2-methoxy-1-pent-2-ynyloxy-benzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (3-methoxy-4-pent-2-ynyloxy-phenyl)-methanol (27 g, 0.12 mol) in 450 ml of dioxan is added dropwise to 240 ml of concentrated hydrochloric acid. The reaction mixture is stirred for 1.5 hours at room temperature. Subsequently it is poured on water and extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate and evaporated in vacuo to obtain 4-chloromethyl-2-methoxy-1-pent-2-ynyloxy-benzene as yellow oil.

Workup

  1. additionSubsequently it is poured on water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7a630b6eee2b467e860d1d0089b0a612
Source dataset
uspto-grants-2007_03
Patent number
US07189873B2

Reaction notes

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