Acetals from Alcohols and Aldehydes
1683
2
IR (neat): n (cm ) 3437, 3126, 2931, 2889, 1723, 1504, 1363, 1230, 1155,
1
1
1
097, 884, 749. H NMR (300 MHz, CDCl ): d 2.45 (s, 1H, OH), 3.63–3.68
3
(m, 5H, CH CHCH OH), 5.90 (s, 1H, CHO ), 6.36 (m, 1H, OCHCHCHC),
2 2 2
6
.45 (m, 1H, OCHCHCHC), 7.43 (m, 1H, OCHCHCHC), 2.46 (s, 1H, OH),
.04–4.23 (m, 5H, CH CHCH OH), 6.04 (s, 1H, CHO ), 6.37 (m, 1H,
4
OCHCHCHC), 6.50 (m, 1H, OCHCHCHC), 7.45 (m, 1H, OCHCHCHC) ppm.
2
2
2
2-(5-Methyl-furan-2-yl)-[1,3]dioxolane (3f). This compound was prepared
in the same manner as that described previously. This pure product (3f) is a
2
1
colorless liquid: 74–758C/0.80 KPa, C H O . IR (neat): n (cm ) 3111,
2
8
10 3
1
955, 2890, 1726, 1616, 1565, 1383, 1349, 1219, 1110, 945, 791. H NMR
(300 MHz, CDCl ): d 2.30 (s, 3H, CH CO), 3.97–4.05 (m, 2H,
OCH CH O), 4.12–4.16 (m, 2H, OCH CH O), 5.84 (s, 1H, CHO ), 5.93
3
3
2
2
2
2
2
(
m, 1H, CH CCHCH), 6.33 (d, J ¼ 3.12 Hz, 1H, CH CCHCH) ppm.
3
3
4-Methyl-2-(5-methyl-furan-2-yl)-[1,3]dioxolane (3g). This compound was
prepared in the same manner as that described previously. This pure product
(
3g, isomers) is a yellow liquid: 97–998C/0.80 KPa, C H O . IR (neat):
9
12 3
2
n (cm ) 3438, 2981, 2938, 1724, 1678, 1565, 1521, 1382, 1187, 967, 794.
1
1
H NMR (300 MHz, CDCl ): d 1.32 (d, J ¼ 6.12 Hz, 3H, OCHCH ), 2.30
3
3
(
(
(
(
(
(
s, 3H, CH CO), 3.50 (m, 1H, OCH H ), 4.09 (m, 1H, OCH H ), 4.28
3 a b a b
m, 1H, OCHCH ), 5.82 (s, 1H, CCHO ), 5.93 [m, 1H, CHC(CH )O], 6.30
3
2
3
d, J ¼ 3.09 Hz, 1H, CHCO), 1.39 (d, J ¼ 6.06 Hz, 3H, OCHCH ), 2.30
3
s, 3H, CH CO), 3.61 (m, 1H, OCH H ), 4.23 (m, 1H, OCH H ), 4.42
3
a
b
a b
m, 1H, OCHCH ), 5.95 (s, 1H, CCHO ), 5.91 [m, 1H, CHC(CH )O], 6.35
3
2
3
d, J ¼ 3.12 Hz, 1H, CHCO) ppm.
4-Chloromethyl-2-(5-methyl-furan-2-yl)-[1,3]dioxolane(3h).Thiscompound
was prepared in the same manner as that described previously. This pure
product (3h, isomers) is a pale yellow liquid: 129–1318C/1.86 KPa,
2
C H ClO . IR (neat): n (cm ) 3492, 2957, 2887, 1728, 1565, 1431, 1351,
1
9
11
3
1
1
220, 1174, 1093, 1021, 946, 792. H NMR (300 MHz, CDCl ): d 2.29
3
(
(
(
(
(
(
m, 3H, CH C), 3.56 (m, 1H, CH H Cl), 3.64 (m, 1H, CH H Cl), 3.93
3 a b a b
m, 1H, OCH H ), 4.12 (m, 1H, OCH H ), 4.30 (m, 1H, OCHCH Cl), 5.84
2
a
b
a
b
s, 1H, CCHO ), 5.93 (m, 1H, CHCHCO), 6.32 (m, 1H, CHCO); 2.30
2
m, 3H, CH C), 3.60 (m, 1H, CH H Cl), 3.67 (m, 1H, CH H Cl), 4.09
a b
3
a
b
m, 1H, OCH H ), 4.30 (m, 1H, OCH H ), 4.52 (m, 1H, OCHCH Cl), 5.99
a
b
a
b
2
s, 1H, CCHO ), 5.95 (m, 1H, CHCHCO), 6.38 (m, 1H, CHCO) ppm.
2
2-(5-Methyl-furan-2-yl)-[1,3]oxathiolane (3i). This compound was prepared
in the same manner as that described previously. This pure product (3i) is an
2
1
aurantium liquid: 120–121 8C/1.20 KPa, C H O S. IR (neat): n (cm
2
)
943, 2873, 1559, 1385, 1222, 1162, 1056, 1021, 966, 947, 788. H NMR
8
10 2
1
(
300 MHz, CDCl ): d 2.29 (s, 3H, CH CO), 3.07–3.27 (m, 2H, SCH CH ),
3
3
2
2
3
CHC(CH )O], 6.34 (m, 1H, CHCO) ppm.
.98–4.34 (m, 2H, OCH CH ), 6.05 (s, 1H, CHSO), 5.92 [m, 1H,
2 2
3