Water → HCID 59518034, compound

HRID 537443Notes

Reaction equation

HRID 537443 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH3:19][C:20]([CH3:25])([CH3:24])[CH2:21][CH:22]=[O:23].O>O1CCCC1>[OH:23][CH:22]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)[CH2:21][C:20]([CH3:25])([CH3:24])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 69273Methyl 4-iodobenzoateHCID 763353,3-DimethylbutanalHCID 178461733HCID 178461733, compound

Product 1

HCID 59518034HCID 59518034, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a −40° C. solution of methyl 4-iodobenzoate (1 g, 4 mmol) in tetrahydrofuran (10 mL) was added isopropylmagnesium chloride lithium chloride (3.82 mL, 1.3 M in THF, 4.98 mmol). The mixture was stirred at −40° C. for 30 minutes, 3,3-Dimethylbutanal (573 mg, 2.86 mmol) was added. The reaction was stirred at room temperature for 4 hours. Water (10 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave (+/−)-methyl 4-(1-hydroxy-3,3-dimethylbutyl)benzoate (640 mg, 95%). 1H NMR (400 MHz, CDCl3, δ): 7.93 (d, 2H), 7.34 (d, 2H), 4.81-4.84 (m, 1H), 3.84 (s, 3H), 1.70-1.61 (m, 1H), 1.53-1.49 (m, 1H), 0.94 (s, 9H).

Workup

  1. stirringThe reaction was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-0cf88f30d54146839bf38d8369a6c476
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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