4-Hydroxybenzyl Alcohol → HCID 131720747, compound

HRID 965269Notes

Reaction equation

HRID 965269 reaction equation
C[O-].[Na+].[OH:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20](Br)[SiH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=1>CN(C=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([SiH:21]([CH3:23])[CH3:22])[O:4][C:5]2[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 10942334Sodium MethoxideHCID 131720746HCID 131720746, compound

Product 1

HCID 131720747HCID 131720747, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (4.17 g, 73.4 mmole) was added under argon to a solution of 4-hydroxybenzyl alcohol (8.67 g, 69.9 mmol) in dry DMF (70 mL) and the reaction mixture was stirred for 30 minutes at room temperature. 4-Bromophenyldimethylsilylmethyl-bromide (22.6 g, 73.4 mmol) was added through a canula and the reaction was stirred at RT for 30 minutes and at 65° C. for 45 minutes. The reaction was poured into ice water (250 mL) and extracted with ethyl acetate. The combined extracts were washed with water, 5% sodium bicarbonate and brine and the dried (Na2 SO4). The solution was concentrated to an oil at reduced pressure and purified by flash chromatography (silica gel, 20% ethyl acetate/hexane) to yield the product as a clear, colorless oil (9.23 g, 38%). 1H NMR (400 MHz, CDCl3) 7.48 (dd, 4H), 7.10 (dd, 4H), 4.61 (s, 2H), 3.77 (s, 2H), 0.42 (s, 6H).

Workup

  1. stirringthe reaction was stirred at RT for 30 minutes and at 65° C. for 45 minutes
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water, 5% sodium bicarbonate and brine
  4. customthe dried (Na2 SO4)
  5. concentrationThe solution was concentrated to an oil at reduced pressure
  6. custompurified by flash chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-84880cfdc36448b7815f0b17765cb6ae
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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