Ammonium Chloride → 4-(2',5'-Dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol

HRID 247634Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]([O:14][CH3:15])=[C:8]([CH3:16])[C:4]=1[CH2:5][Mg]Br.C1[O:22][CH:18]1[C:19](=[CH2:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]([O:14][CH3:15])=[C:8]([CH3:16])[C:4]=1[CH2:5][CH:20]=[C:19]([CH3:21])[CH2:18][OH:22]

Participants

Conditions

Temperature: -78 °C

Procedure

26.7 mmol of 2,5-dimethoxy-3,4,6-trimethylbenzylmagnesium bromide were treated at -78° C. with 3.6 g of lithium tetrachlorocuprate (Li2CuCl4) as a 0.1 molar solution in tetrahydrofuran. 2.2 g (26 mmol) of isoprene oxide were subsequently added. The mixture was thereupon stirred at -78° C. for 1 hour and at room temperature for 3-4 hours. 10 ml of saturated ammonium chloride were then added at 0° C. and the mixture was extracted with ether. After drying the ether extract over sodium sulphate, concentration and crystallization from ethyl ether at -20° C., there were obtained 4.7 g (75%) of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol with a melting point of 85°-86° C.

Workup

extractionthe mixture was extracted with ether
dry with materialAfter drying the ether
extractionextract over sodium sulphate, concentration and crystallization from ethyl ether at -20° C.

Sources & evidence

ORD record: ord-47be02ac101c42bfa5fa95737ec381b2
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04709055

Reaction notes

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