Carbon Dioxide → (3,5-Diethylphenyl)methanol

HRID 409377Notes

Reaction equation

HRID 409377 reaction equation
[C:1](=[O:3])=O.Br[C:5]1[CH:6]=[C:7]([CH:10]=[C:11](Br)C=1)[CH2:8]O.[Zn](CC)CC.Cl.[CH2:20]1[CH2:24]O[CH2:22][CH2:21]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCOC(C)=O.CCCCCCC>[CH2:21]([C:20]1[CH:24]=[C:5]([CH2:1][OH:3])[CH:6]=[C:7]([CH2:10][CH3:11])[CH:8]=1)[CH3:22]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 7009423(3,5-Dibromophenyl)methanolHCID 178418750HCID 178418750, compound2×

Product 1

HCID 54364779(3,5-Diethylphenyl)methanolYield 53%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21899848Ethylacetate heptaneSolvent2×

Procedure

To a cooled (dry ice) mixture of 3,5-dibromobenzyl alcohol (1 g, 3.8 mmol) and PdCl2(dppf) [0.07 eq] in dry THF (10 mL) was added 1.1 M Et2Zn (15 mL, 16 mmol, 4.4 eq). The resulting mixture was allowed to warm to RT, stirred at 45° C. (programmed block temperature, overnight). To bring the reaction to completion (disappearance of both starting material and monoalkylated product) additional 1.1 M Et2Zn (10 mL, 11 mmol, 2.9 eq) was added with continued stirring at 45° C. (again overnight). After cooling, the reaction mixture was then added to a stirred mixture of dilute HCl and heptane/EtOAc (2:1; ˜200 mL), and the organic layer was dried (Na2SO4), filtered, and evaporated. Chromatography (10% EtOAc/heptane) gave 0.33 g (yield of 53%) of title product. 1H NMR (300 MHz, CDCl3) δ 1.22 (t, 6H), 1.65 (br s, 1H), 2.61 (q, 4H), 4.66 (s, 2H), 6.95-7.05 (m, 3H).

Workup

  1. temperatureTo a cooled
  2. additionwas added
  3. stirringwith continued stirring at 45° C. (again overnight)
  4. temperatureAfter cooling
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c9266f5f1d73425b9b556877b74c7dfa
Source dataset
uspto-grants-2014_06
Patent number
US08759340B2

Reaction notes

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