Water → 5-(1,1-Dimethyl-allyl)-2-hydroxy-benzaldehyde

HRID 30614Notes

Reaction equation

HRID 30614 reaction equation
B(Cl)(Cl)Cl.[CH3:5][C:6]([C:10]1[CH:11]=[CH:12][C:13]([O:18]C)=[C:14]([CH:17]=1)[CH:15]=[O:16])([CH3:9])[CH:7]=[CH2:8].O>C(Cl)Cl>[CH3:9][C:6]([C:10]1[CH:11]=[CH:12][C:13]([OH:18])=[C:14]([CH:17]=1)[CH:15]=[O:16])([CH3:5])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 113331815-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

Product 1

HCID 858888685-(1,1-Dimethyl-allyl)-2-hydroxy-benzaldehydeYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron trichloride (1M in CH2Cl2, 39.7 mmol) was added dropwise under argon at −78° C. to a stirred solution of 5-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde (13.2 mmol) in dry CH2Cl2 (120 ml). The dry ice—acetone bath was removed and reaction allowed warming to RT. Stirred at RT for 18 hours, before the reaction mixture was cooled to 0° C. and iced water (125 ml) slowly added. Extracted with CH2Cl2 (2×100 ml). The organic phases were washed with brine, dried (Na2SO4), filtered, and evaporated to black oil. Purified by flash chromatography (heptane:EtOAc) to give the title product as yellow oil in 56% yield. 1H-NMR (CDCl3) δ 10.82 (s, 1H), 9.81 (s, 1H), 7.43 (d, 1H), 7.41 (s, 1H), 6.86 (d, 1H), 5.92 (dd, 1H), 5.02-4.96 (m, 2H), 1.34 (s, 6H).

Workup

  1. customThe dry ice—acetone bath was removed
  2. customreaction
  3. temperaturewas cooled to 0° C.
  4. extractionExtracted with CH2Cl2 (2×100 ml)
  5. washThe organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to black oil
  9. customPurified by flash chromatography (heptane:EtOAc)

Sources & evidence

ORD record
ord-3304310e3731466ba7069aac7f5d23b4
Source dataset
uspto-grants-2008_09
Patent number
US07423181B2

Reaction notes

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