Methanesulfonic Acid → HCID 57276568, compound

HRID 1636985Notes

Reaction equation

HRID 1636985 reaction equation
CS(O)(=O)=O.[C:6]1([C:12]#[CH:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH2:17].C[O:25][C:26](OC)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:27]>>[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:17][C:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:13].[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[CH3:27].[C:6]1([C:12]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10821PhenylacetyleneHCID 78008Acetophenone dimethyl acetalHCID 521220Benzene, (1-methoxyethenyl)-2×

Product 3

HCID 7410AcetophenoneYield 4%HCID 119301,1':3',1''-Terphenyl, 5'-phenyl-Yield 2%HCID 57276568HCID 57276568, compoundYield 13%

Conditions

Temperature
40 °C

Procedure

In a flask equipped with thermometer and reflux condenser, methanol (8.01 g, 250 mmol) and phenylacetylene (6.38 g, 62.5 mmol) were provided and heated to 40° C. Triphenylphosphine gold(I) methyl (14.8 mg, 31.2 μmol) and methanesulfonic acid (40.6 μl, 625 μmol) were then added in rapid succession. After a reaction time of 8 h, 99% of the phenylacetylene had been converted. The main products formed were α-methoxystyrene (selectivity (S)=61%) and acetophenone dimethyl ketal (S=20%). Subsequent acid-catalyzed reaction of the α-methoxystyrene by-produced 1-methoxy-1,3-diphenylbutadiene (as 1:1 cis/trans mixture, S=13%) acetophenone (S=4%) and 1,3,5-triphenylbenzene (S=2%).

Workup

  1. customThe main products formed

Sources & evidence

ORD record
ord-548342e771934e52a863124fb6fd9dbf
Source dataset
uspto-grants-2000_03
Patent number
US06037482

Reaction notes

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