Toluene → HCID 86613081, compound

HRID 1869141Notes

Reaction equation

HRID 1869141 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH:9]2[CH2:11][O:10]2)=[CH:5][CH:4]=1.[Cl:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:20]=[C:19]([Cl:29])[C:18]=1[OH:30].C1(C)C=CC=CC=1>C(N(C(C)C)C(C)C)C>[Cl:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:20]=[C:19]([Cl:29])[C:18]=1[O:30][CH2:11][CH:9]([OH:10])[CH2:8][O:7][C:6]1[CH:12]=[CH:13][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 222827522-((4-(Trifluoromethyl)phenoxy)methyl)oxirane

Product 1

HCID 86613081HCID 86613081, compound

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

8 g of 2-(4-trifluoromethyl-phenoxymethyl)-oxirane and 3.8 g of 2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenol are stirred in 80 ml of N-ethyl-diisopropylamine and 50 ml of toluene for 14 days at 100° C. The reaction mixture is concentrated, and the residue is taken up in ethyl acetate and washed with hydrochloric acid and water. After concentration of the organic phase and purification over silica gel, 1-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-3-(4-trifluoromethyl-phenoxy)-propan-2-ol is obtained. 1H-NMR (CDCl3) 300 MHz: 2.81 (d, 1H), 4.15-4.48 (m, 5H), 4.59 (d, 2H), 6.11 (t, 1H), 6.86 (s, 2H), 7.01 (d, 2H), 7.58 (d, 2H)

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washwashed with hydrochloric acid and water
  3. customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record
ord-c41ed5f1e94042ca8ab64bd8ca636ff3
Source dataset
uspto-grants-2009_12
Patent number
US07638514B2

Reaction notes

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