Ammonia → HCID 53441801, compound
Reaction equation
[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:13])=[CH:7]/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11].[C-]#[C-].[Na+].[Na+].N.S(=O)(=O)(O)[O-].[PH4+].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:27]=1.S(=O)(=O)(O)O.[PH4+]>>[CH3:12][C:10]([OH:11])([CH:9]=[CH:8][CH:7]=[C:6]([CH3:13])[CH2:5][CH2:4][CH:3]=[C:2]([CH3:14])[CH3:1])[CH:26]=[CH2:27]Participants
Procedure
3,7,11-Trimethyl-dodeca-1,4,6,10-tetraen-3-ol is prepared, as described in German Pat. No. 1,115,238, from pseudo-ionone by a reaction with sodium acetylide in liquid ammonia followed by hydrogenation of the triple bond. Using the conventional method described in German Pat. No. 1,068,710, the product is then converted to the phosphonium bisulfate by means of triphenylphosphine and sulfuric acid. This phosphonium salt is reacted with β-formylcrotyl acetate by the method described in German Pat. No. 1,068,710 to give 1-acetoxy-3,7,11,15-tetramethyl-hexadecy-2,4,6,8,10,14-hexaene. This ester is reacted with triphenylphosphine and sulfuric acid as described in German Pat. No. 1,068,709 to give crystalline 3,7,11,15-tetramethyl-hexadeca-2,4,6,8,10,14-hexaen-1-yl-triphenylphosphonium bisulfate. Melting point 150°-155° C.
Sources & evidence
- ORD record
- ord-9c0816314b924638aefaf81d18695f36
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04127455
Reaction notes
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