HCID 86754148, compound → HCID 21711985, compound

HRID 580802Notes

Reaction equation

C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][O:28][C:29](=[O:65])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:25])C=CC=CC=1>C(O)(=O)C>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][O:28][C:29](=[O:65])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][OH:45])=[O:25]

Participants

Conditions

Temperature: 55 °C

Procedure

Methylene bis(16-triphenylmethoxyhexadecanoate) (0.07 g, 0.07 mmol) is dissolved in glacial acetic acid (8 ml) and heated at 55° C. The reaction is monitored by TLC. After 10 hours the reaction mixture is poured onto ice, and the crude product is filtered, washed with aqueous sodium bicarbonate and water, and dried under reduced pressure. The product is purified by flash chromatography on a silica column with chloroform/methanol (20:1) as eluant to yield the title compound as a white solid. 1H-NMR (300 MHz, CDCl3): δ 1.2-1.4(m, 44H), 1.5-1.6(m, 8H), 2.35(t, 4H), 3.64(t, 4H), 5.75(s, 2H).

Workup

additionAfter 10 hours the reaction mixture is poured onto ice
filtrationthe crude product is filtered
washwashed with aqueous sodium bicarbonate and water
customdried under reduced pressure
customThe product is purified by flash chromatography on a silica column with chloroform/methanol (20:1) as eluant

Sources & evidence

ORD record: ord-6fdac8195a5a4679a381adac6d5ec61a
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919753

Reaction notes

Loading…