Phthalic Acid → HCID 12362163, compound

HRID 1390542Notes

Reaction equation

HRID 1390542 reaction equation
C(O)C=C.[CH2:5]([OH:9])[CH:6]([CH3:8])[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:29]([OH:40])(=O)[C:30]1[C:31](=CC=CC=1)[C:32](O)=O>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Rh].[Rh].[Rh].[Rh].[Rh].[Rh]>[CH2:5]([O:9][CH:29]1[CH2:30][CH2:31][CH2:32][O:40]1)[CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 1017Phthalic AcidHCID 6560IsobutanolHCID 7858Allyl AlcoholHCID 11776Triphenylphosphine

Product 1

HCID 12362163HCID 12362163, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1086604328407-51-4Catalyst

Procedure

The autoclave is charged with 50.0 g. of allyl alcohol (861 mmol.), 111.7 g. of isobutanol (1.50 mol.). 0.202 g. of hexarhodium hexadecacarbonyl (0.189 mmol.. 1.14 meq. Rh), 9.6 of triphenylphosphine (36.6 mmol.) and 2.86 g. of phthalic acid (17.2 mmol.), then heated at 125° C. under replenished 800-1200 psi 1:1 H2 /CO for one hour. Quantitative glpc analysis of the product mixture shows the presence of 61.0 g. 2-isobutoxytetrahydrofuran (49% yield) identified based on ir, nmr. and mass spectra which are in complete accord with the assignment. Another product present in relatively minor amount is isolated and identified as 3-(α-tetrahydrofuranyloxy)-2-methyl-propionaldehyde on the basis of its i r spectrum.

Workup

  1. additionThe autoclave is charged with 50.0 g
  2. customfor one hour

Sources & evidence

ORD record
ord-a1d970cdc6a04988a3485e228b939032
Source dataset
uspto-grants-1979_02
Patent number
US04139542

Reaction notes

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