2-(Benzyloxy)-3-(tert-butyl)benzaldehyde → (2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)methanol

HRID 1042518

Reaction equation

HRID 1042518 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:1]([O:8][C:9]1[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 115435672-(Benzyloxy)-3-(tert-butyl)benzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 58238520(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)methanolYield 78%

Procedure

A solution of 2-(benzyloxy)-3-tert-butylbenzaldehyde (5.4 g, 20 mmol) was stirred under nitrogen on an ice bath and 1M phenyl magnesium bromide (30 mL, 1.5 equiv) was added at such a rate that temperature did not exceed 7° C. Stirring was continued at room temperature for 2 hr. The reaction mixture was cooled on an ice bath and quenched with saturated ammonium chloride (50 mL). The resulting mixture was partitioned between water (25 mL) and 1:1 ethyl acetate/heptane (150 mL). The organic layer was washed with brine (100 mL), dried over sodium sulfate and the solvent was removed in a rotary evaporator. The crude product (7.3 g) was purified by chromatography on silica (75 g) with heptane (0.5 L) and 2.5% ethyl acetate in heptane (2 L) to produce 13 (5.4 g, 78%) as a pale yellow oil.

Workup

  1. customdid not exceed 7° C
  2. temperatureThe reaction mixture was cooled on an ice bath
  3. customquenched with saturated ammonium chloride (50 mL)
  4. customThe resulting mixture was partitioned between water (25 mL) and 1:1 ethyl acetate/heptane (150 mL)
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed in a rotary evaporator
  8. customThe crude product (7.3 g) was purified by chromatography on silica (75 g) with heptane (0.5 L) and 2.5% ethyl acetate in heptane (2 L)

Sources & evidence

ORD record
ord-4ffe47f735e94753b80e77dbfcd1a54d
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Linked notes

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