Isobutylene oxide → HCID 86697121, compound

HRID 237456Notes

Reaction equation

HRID 237456 reaction equation
[CH3:1][C:2]1([CH3:5])[CH2:4][O:3]1.[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[CH:9][C:8]=1[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([O:14][CH2:1][C:2]([CH3:5])([OH:3])[CH3:4])=[CH:9][C:8]=1[CH3:15]

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 86697121HCID 86697121, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a microwave vial 2,2-dimethyloxirane (2.2 g) is added to a suspension of 4-bromo-3,5-dimethylphenol and K2CO3 (11 g) in N,N-dimethylformamide (6 mL). The vial is sealed and the mixture is heated for 48 hours to 120° C. After cooling to room temperature the mixture is partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→50:50) to give the title compound. Yield: 2.9 g; LC (method 4): tR=1.76 min; Mass spectrum (ESI+): m/z=273 [M+H]+.

Workup

  1. customThe vial is sealed
  2. temperaturethe mixture is heated for 48 hours to 120° C
  3. customis partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
  4. extractionThe aqueous phase is extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases are dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→50:50)

Sources & evidence

ORD record
ord-7de8c6cf47f54171980976c30564496e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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