6-Chlorobenzo[d][1,3]dioxole-4-carbaldehyde → 1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanol

HRID 2426056Notes

Reaction equation

HRID 2426056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[CH3:13][Mg+].[Br-]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]([OH:12])[CH3:13])[C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 587073116-Chlorobenzo[d][1,3]dioxole-4-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 587073141-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

6-Chlorobenzo[d][1,3]dioxole-4-carbaldehyde (147.0 mg, 0.79 mmol) was dissolved in 6 mL of diethyl ether and cooled to 0° C. MeMgBr (0.60 mL, 1.99 mmol) was added to the solution and the ice bath was removed. The reaction was allowed to stir at rt for 10 min. and at reflux for 30 min. The reaction was cooled to 0° C. and 10 mL of sat NH4Cl were added to quench the reaction. The diethyl ether layer was separated and washed with water (10 mL×2). The organic layer was dried over Na2SO4 and the solvent was removed by rotary evaporation to collect the desired product (155.0 mg, 98%). 1H NMR (400 MHz, CDCl3): δ 6.90 (d, 1H), 6.75 (d, 1H), 6.01 (d, 2H), 4.96 (m, 1H), 1.50 (d, 3H).

Workup

  1. customthe ice bath was removed
  2. temperatureat reflux for 30 min
  3. temperatureThe reaction was cooled to 0° C.
  4. addition10 mL of sat NH4Cl were added
  5. customto quench
  6. customthe reaction
  7. customThe diethyl ether layer was separated
  8. washwashed with water (10 mL×2)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. customthe solvent was removed by rotary evaporation
  11. customto collect the desired product (155.0 mg, 98%)

Sources & evidence

ORD record
ord-4423612db6774ff794c0600a5a8d7a27
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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