Potassium Carbonate → Dimethyl 4-[3-(4-methoxymethoxy-3-methylphenyl)propyl]phthalate

HRID 970838Notes

Reaction equation

HRID 970838 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][O:12][CH2:13]C)=[C:6]([CH3:15])[CH:5]=1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.FC(F)(F)S(O[C:31]1[CH:32]=[C:33]([C:41]([O:43][CH3:44])=[O:42])[C:34](=[CH:39][CH:40]=1)[C:35]([O:37][CH3:38])=[O:36])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>P[C-]1C=CC=C1.[C-]1(P)C=CC=C1.[Fe+2].Cl[Pd]Cl>[CH3:13][O:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH2:3][C:40]2[CH:39]=[C:34]([C:35]([O:37][CH3:38])=[O:36])[C:33](=[CH:32][CH:31]=2)[C:41]([O:43][CH3:44])=[O:42])=[CH:5][C:6]=1[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 179830711-(Ethoxymethoxy)-2-methyl-4-(prop-2-en-1-yl)benzeneHCID 190893441,2-Dimethyl 4-(trifluoromethanesulfonyloxy)benzene-1,2-dicarboxylate

Product 1

HCID 17983092Dimethyl 4-[3-(4-methoxymethoxy-3-methylphenyl)propyl]phthalate

Reagents, catalysts & solvents 1

HCID 178527691HCID 178527691, compoundCatalyst

Procedure

In a manner similar to Example 1e, by reacting 4.5 g (21.6 mmol) of 4-allyl-1-ethoxymethoxy-2-methylbenzene with 6.3 g (25.7 mmol) of 9-BBN, 7.4 g (21.6 mmol) of dimethyl 4-trifluoromethanesulphonyloxyphthalate, 5.9 g (42.6 mmol) of potassium carbonate and 880 mg (1.05 mmol) of dichloropalladium diphosphinoferrocene. A yellow oil is obtained (m=7 g, y=80%).

Workup

  1. customA yellow oil is obtained (m=7 g, y=80%)

Sources & evidence

ORD record
ord-b9bccb856f354f35866e50b586285436
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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