1,3-Benzenedimethanol

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General procedure: To a solution of the substrate (1 mmol) in ethanol as asolvent (5 mL) in a round-bottomed flask (25 mL) equippedwith a magnetic stirrer, P(BVP)BH4 (100 mg) was addedand stirred at room temperature. The progress of thereaction was monitored by TLC. On completion of thereaction, the mixture was filtered and the used reagent waswashed successively with HCl (1.0 M, 2 10 mL) andethanol (2 5 mL). The combined filtrates were evaporatedand the pure product was obtained in moderate to excellent yields. In a few cases in which the reaction wasnot complete, the crude product was purified on silica gelwith an appropriate eluent (Scheme 1).General procedure: Fe(BFTo a stirred THF (40 mL) solution of isophthalaldehyde (0.27 g, 2.0 mmol) was slowlyadded NaBH4 (0.30 g, 7.9 mmol). To the mixture was slowly added EtOH (10 mL) andthe resulting mixture was stirred at room temperature for 3 h. To the solution was slowlyadded ice water (10 mL) at 0 °C followed by 10percent HCl aq until reaching a pH<7. Themixture was extracted with Et2O (50 mL x 5). The combined organic layers werewashed with brine (50 mL x 5), dried over Na2SO4, filtered and concentrated in vacuo togive benzene-1, 3-dimethanol (7a, 0.25 g, 69percent yield). The resultingsolution was stirred at reflux for 2 h. To the solution was added THF (100 mL) solutionof 1, 3-bis(bromomethyl)benzene (8a, 1.53 g, 5.7 mmol), and the mixture was stirred atreflux for 2 days. To the solution was added ice water (20 mL) at<10 °C. The mixturewas extracted with Et2O (50 mL x 3). The combined organic layers were washed withbrine (50 mL x 3), dried over Na2SO4, filtered, and concentrated in vacuo, giving aresidue that was subjected to silica gel column chromatography (three times, eacheluent; hexane:AcOEt = 1:1, hexane:CHCl3 = 10:1, CHCl3:AcOEt = 20:1) followed byrecrystallization from CH2Cl2/hexane gave 2, 11-dioxa[3.3]metacyclophane (6a, 0.01 g, 7percent yield). Colorless solid; mp 115-117 °C.General procedure: Hydrogenation of Other Ester Compounds Catalyzed by Synthetic Preparation of Bipyridine Tetradshed Ruthenium Complex 5 The results are shown in Table 2:Table 2 Hydrogenation of other ester compounds a; A Reaction conditions: S / C = 1000, 3.0 mmol Substrate, 3.0 μmol 5, 3.0 mL lPrOH, 0.3 mmol NaOMe, 5 MPa H2, 25 ° C. F Tetrahydrofuran as solvent.Under Ar atmosphere, to dimethyl isophthalate (2.00 g, 10.30 mmol) were added dry THF (51.5 mL, 0.2M solution) and lithium borohydride (1.12 g, 51.5 mmol, 5 eq.), and stirred for 23 hours. Then, in an ice bath, to the mixture was added a few drops of acetic acid to neutralize the mixture, thereby quenching the reaction. The mixture was stirred for a while. Formed crystals were dissolved by adding MeOH. Although there was one spot of product as checked by TLC (Hex:EtOAc=1:1) during the reaction, after the reaction quenched, there were two spots of products on TLC. The solvent was distilled off under reduced pressure. Products were separated by silica gel column chromatography (only EtOAc) to give a compound (11) (1.36 g, 9.82 mmol, 95percent). [0030] In a stainless steel pressure resistant vessel having an inner capacity of 40 mL equipped with a thermometer and a manometer, 0.30 g of m-xylylenediamine, 7.50 g of methanol and 0.10 g of sodium hydroxide were charged, and the vessel was sealed under a nitrogen atmosphere. The mixture was heated and held at 240°C for 2 hours. After cooling, the reaction solution was taken out, and after neutralizing sodium hydroxide, was analyzed. The conversion ratio of m-xylylenediamine was 100percent, and the yield of m-xylylene glycol was 73percent. Examples 41 to 43 Investigation of Addition of Water [0043] The reaction was performed in the same manner as in except that water was added at the ratios shown in Table 6. The results are shown in Table 6 along with Example 1.

Molecular Weight:138.16
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:138.068079557
Monoisotopic Mass:138.068079557
Topological Polar Surface Area:40.5
Heavy Atom Count:10
Complexity:83.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes