Methanol → (2-Methoxyethyl)benzene

HRID 1584068Notes

Reaction equation

HRID 1584068 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][OH:11]>>[CH3:10][O:11][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 7666Phenethyl bromide

Product 1

HCID 19089(2-Methoxyethyl)benzene

Conditions

Temperature
149 °C

Procedure

A mixture of (2-bromoethyl)benzene (2.0 g) and methanol (60 mL) in a PEEK vessel equipped with a magnetic stirrer bar was placed into the reactor, and the cover sealed. The mixture was stirred and heated to 149° C. (1.08 MPa) within 10 min and held at this temperature for 2 hours. Samples were withdrawn periodically and analysed. The mixture was then cooled. After 1 hour the conversion to (2-methoxyethyl)benzene was 50% increasing to 80% after 2 hours. GC/MS: m/z (rel.int. %) 136(M +, 13), 104(8), 91(28), 77(6), 65(11), 63(4), 51(9), 50(4), 45(100). 1H NMR, (CDCl3 ; 200 MHz): δ7.23, m, 5H, Ar; 3.6, t, 2H, --CH2 --O--CH3 ; 3.4, s, 3H, --O --CH3 ; 2.9, t, 2H, Ar--CH2 --.

Workup

  1. customequipped with a magnetic stirrer bar
  2. customthe cover sealed
  3. customSamples were withdrawn periodically
  4. temperatureThe mixture was then cooled
  5. waitAfter 1 hour the conversion to (2-methoxyethyl)benzene was
  6. temperature50% increasing to 80% after 2 hours

Sources & evidence

ORD record
ord-84f17a1625a040b0837196f9e46f097f
Source dataset
uspto-grants-1999_08
Patent number
US05932075

Reaction notes

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