p-Toluenesulfonic acid monohydrate → 1-(4-Methoxyphenyl)propan-2-ol

HRID 1516954Notes

Reaction equation

HRID 1516954 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2([CH3:13])OCC[O:9]2)=[CH:5][CH:4]=1.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O.C(OCC)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]([OH:9])[CH3:13])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 3423265Sodium Lauryl SulfateHCID 126421502-[(4-Methoxyphenyl)methyl]-2-methyl-1,3-dioxolaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1691451-(4-Methoxyphenyl)propan-2-olYield 86.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

2-(4-Methoxybenzyl)-2-methyl-1,3-dioxolane (0.64 g, 3 mmol), sodium dodecyl sulfate (0.2 g, 0.7 mmol) and a stir bar were added to the inside of a PDMS thimble. p-Toluene sulfonic acid monohydrate (0.145 g, 0.8 mmol) dissolved in 4 mL water was added to the inside of the PDMS thimble followed by 2 mL of THF. The reaction was stirred at 25° C. for 5 hours. LiAlH4 (0.229 g, 6 mmol) and 5 mL hexanes were added to the outside of the PDMS thimble and the reaction proceeded for 24 hours. 5 mL Water was added. The PDMS thimble was swelled with 20 mL hexanes and 2×20 mL diethyl ether, the organics were combined and dried over MgSO4 and evaporated. The product was purified by flash chromatography eluting with 1:4 ethyl acetate:hexanes to yield a pale yellow oil (0.43 g, 83% yield). 1H NMR (CDCl3): δ 1.22 (d, J=5.7 Hz, 3H), 1.69 (s, 1H), 2.61 (dd, J=13.2, 7.5 Hz, 1H), 2.72 (dd, J=13.5, 4.8 Hz, 1H), 3.78 (s, 3H), 3.93-3.98 (m, 1H), 6.85 (d, J=8.4, 2H), 7.12 (d, J=8.7 Hz, 2H). 13C NMR (CDCl3): δ 22.61, 44.77, 55.18, 68.88, 113.89, 130.27, 130.43, 158.19.

Workup

  1. waitthe reaction proceeded for 24 hours
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe product was purified by flash chromatography
  5. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-10d42067605b4da49f7beae852c0f9c5
Source dataset
uspto-grants-2012_07
Patent number
US08227635B2

Reaction notes

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