Sulfuric Acid → HCID 88304998, compound

HRID 2419478Notes

Reaction equation

HRID 2419478 reaction equation
C(O[CH2:5][CH:6]=[C:7]([CH3:24])[CH:8]=[CH:9][CH:10]=[C:11]([CH3:23])[CH:12]=[CH:13][CH:14]=[C:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])(=O)C.[C:25]1([P:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[S:44](=[O:48])(=[O:47])([OH:46])[OH:45]>>[S:44](=[O:46])(=[O:45])([OH:48])[O-:47].[CH3:24][C:7]([CH:8]=[CH:9][CH:10]=[C:11]([CH3:23])[CH:12]=[CH:13][CH:14]=[C:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:20])[CH3:21])=[CH:6][CH2:5][P+:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 53973276HCID 53973276, compound

Product 1

HCID 88304998HCID 88304998, compound

Procedure

3,7,11-Trimethyl-dodeca-1,4,6,10-tetraen-3-ol is prepared in accordance with German Pat. No. 1,115,238 from pseudoionone by reaction with sodium acetylide in liquid ammonia, followed by hydrogenation of the triple bond. The phosphonium bisulfate is prepared therefrom in the conventional manner, according to German Pat. No. 1,068,710, by reaction with triphenylphosphine and sulfuric acid. This phosphonium salt is reacted with β-formylcrotyl acetate, in accordance with German Pat. No. 1,068,710, to give 1-acetoxy-3,7,11,15-tetramethyl-hexadeca-2,4,6,8,10,14-hexaene. Crystalline 3,7,11,15-tetramethylhexadeca-2,4,6,8,10,14-hexaen-1-yl-triphenylphosphonium bisulfate is prepared from this ester, in accordance with German Pat. No. 1,068,709, by reaction with triphenylphosphine and sulfuric acid. Melting point 150° - 155° C.

Sources & evidence

ORD record
ord-1f6ec4222c1942fd83adf6e4166ec872
Source dataset
uspto-grants-1978_08
Patent number
US04105855

Reaction notes

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