Potassium Hydroxide → HCID 53789991, compound
Reaction equation
[CH3:1][CH:2]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:31])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:30])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[C:3](=[O:10])[CH2:4]C(OCC)=O.Br[CH2:33][C:34]([CH3:61])=[CH:35][CH2:36][CH2:37][C:38]([CH3:60])=[CH:39][CH2:40][CH2:41][C:42]([CH3:59])=[CH:43][CH2:44][CH2:45][C:46]([CH3:58])=[CH:47][CH2:48][CH2:49][C:50]([CH3:57])=[CH:51][CH2:52][O:53]C(=O)C.[H-].[Na+].[OH-].[K+]>CCOCC.C(O)C>[CH3:57][C:50]([CH2:49][CH2:48][CH:47]=[C:46]([CH3:58])[CH2:45][CH2:44][CH:43]=[C:42]([CH3:59])[CH2:41][CH2:40][CH:39]=[C:38]([CH3:60])[CH2:37][CH2:36][CH:35]=[C:34]([CH3:61])[CH2:33][CH2:4][C:3](=[O:10])[CH:2]([CH3:1])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:31])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:30])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:51][CH2:52][OH:53]Participants
7
Procedure
As in Example 7 (4), ethyl 3,7,11,15,19-pentamethyl-6,10,14,18-eicosatetraen-2-one-1-carboxylate (4.3 g) and 1-bromo-2,6,10,14,18-pentamethyl-20-acetoxy-2,6,10,14,18-eicosapentaene (4.8 g) are reacted in ether (59 ml) in the presence of sodium hydride (0.26 g). The product is added to a solution of potassium hydroxide (1.68 g) in ethanol (32 ml), and the resultant mixture is treated as in Example 1 (4) to give 3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,26,30,34,38-tetracontanonaen-22-on-1-ol (6.8 g). IR: 3400, 1000 cm-1 (OH); 1705 cm-1 (C=O); 1668 cm-1 (C=C). NMR (carbon tetrachloride): δ 1.59 (s), 1.66 (s), 2.01 (m), 2.7 (m), 4.1 (m), 5.05 (m).
Sources & evidence
- ORD record
- ord-09ddb9d7b70e4a7ca97f3fa937af7fa3
- Source dataset
- uspto-grants-1976_02
- Patent number
- US03939202
Reaction notes
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