4-Methylbenzaldehyde → HCID 54282891, compound

HRID 1491567Notes

Reaction equation

[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[C:10]([C@@H:15]([C@H:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[OH:18])O)([O:12][CH2:13][CH3:14])=[O:11]>>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([CH:7]2[O:18][C@@H:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C@H:15]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:8]2)=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 77254-Methylbenzaldehyde

HCID 6993580Diethyl tartrate

Product 1

HCID 54282891HCID 54282891, compound

Procedure

In a fashion similar to that described in Example 3, p-tolualdehyde was condensed with diethyl L-tartrate to provide (4R,5R)-2-(4-methylphenyl)-4,5-dicarboethoxy-1,3-dioxolane, an oil, GLC analysis: 93%, [α]D25 -9.6° (c,0.1,methanol), 1H-NMR (CDCl3)δ7.47 (2H,d,J=8.0 Hz), 7.18 (2H,d,J=8.0 Hz) 6.12 (1H,s), 4.93 (1H,d,J=4.0 Hz), 4.81 (1H,d,J=7.2 Hz), 4.34-4.22 (4H,2 q, overlapping, J=7.2 Hz), 2.34 (3H, s), 1.35-1.26 (6H 2 t, overlapping, J=7.2 Hz). IR (film) 2980, 1740, 1615 cm-1. MS m/e (% abundance) 308(2), 293(1), 279(1), 235(12), 136(68), 119(100), 105(50), 91(20), 77(8), 43(6).

Sources & evidence

ORD record: ord-e5c6e891f8654b12a37b24cf0fe16ca3
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05371069

Reaction notes

Loading…