5-(4-Benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one → 5-(4-Hydroxy-benzyl)-2,2-dimethyl-(1,3]dioxolan-4-one

HRID 1985260Notes

Reaction equation

HRID 1985260 reaction equation
C([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][CH:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]2=[O:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][CH:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]2=[O:21])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 184437075-(4-Benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one

Product 1

HCID 99208865-(4-Hydroxy-benzyl)-2,2-dimethyl-(1,3]dioxolan-4-oneYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(4-benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one (1.0 g, 3.20 mmol) and 10% Pd/C (0.75 g) in EtOAc (40 mL) was purged with N2 then H2 and then stirred under a H2 balloon atmosphere for 3 h at room temperature. Upon reaction completion, Na2SO4 was added and the mixture filtered through hyflo. The solvent was removed in vacuo to afford 0.747 g (100%) 5-(4-hydroxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one. 1H NMR (500 MHz, CDCl3) δ 7.11 (d, 2H, J=8.31 Hz), 6.76 (d, 2H, J=8.31 Hz), 4.92 (bs, 1H), 4.61 (dd, 1H, J=6.36 Hz, J=4.40 Hz), 3.11 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 2.98 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 1.50 (s, 3H), 1.36 (s, 3H); MS (ES−) Calc'd for C12H13O4 (M−1) 221. Found m/z 221 (100%).

Workup

  1. customwas purged with N2
  2. customUpon reaction completion, Na2SO4
  3. additionwas added
  4. filtrationthe mixture filtered through hyflo
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-56ad272342a54266ba68b859f9e8e32b
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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