Acetic Anhydride → HCID 53811812, compound

HRID 1578824Notes

Reaction equation

HRID 1578824 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:52])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:51])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:50])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:49])[CH2:22][CH2:23][C:24](=[O:48])[CH:25]([CH3:47])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:46])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:45])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:44])[CH2:38][CH2:39][CH:40]=[C:41]([CH3:43])[CH3:42])=[CH:3][CH2:4][OH:5].[C:53](OC(=O)C)(=[O:55])[CH3:54]>N1C=CC=CC=1>[C:53]([O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:52])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:51])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:50])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:49])[CH2:22][CH2:23][C:24](=[O:48])[CH:25]([CH3:47])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:46])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:45])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:44])[CH2:38][CH2:39][CH:40]=[C:41]([CH3:43])[CH3:42])(=[O:55])[CH3:54]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53789991HCID 53789991, compound

Product 1

HCID 53811812HCID 53811812, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 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) in pyridine (1 g), acetic anhydride (3.5 g) is added, and the resultant mixture is allowed to stand at room temperature for 6 hours. The reaction mixture is treated as in Example 7 (5) (a) to give 1-acetoxy-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,26,30,34,38-tetracontanonaen-22-one (6.2 g), which is then similarly reduced. The resultant product (4.7 g) is treated as in Example 1 (5) (a) to give 1-acetoxy-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,26,30,34,38-tetracontanonaen-22ol (1.9 g) as a fraction (1) and 3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,26,30,34,38-tetracontanonaene-1,22-diol (0.8 g) as a fraction (2). The latter is treated with acetic anhydride as above to give 1-acetoxy-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,26,30,34,38-tetracontanonaen-22-ol (0.73 g).

Sources & evidence

ORD record
ord-e0256cf2c5ec4307a6ce51ff2d06ad30
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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