Acetaldehyde → 1-(2-Fluoro-6-methoxyphenyl)ethanol

HRID 622074Notes

Reaction equation

HRID 622074 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1.[CH:15](=[O:17])[CH3:16].Cl>O1CCCC1>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[CH:15]([CH3:16])[OH:17]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 99753-FluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 212933001-(2-Fluoro-6-methoxyphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (3.9 mls of 1.14M in hexane) was added dropwise to a solution of 3-fluoroanisole (0.45 mls) in dry tetrahydrofuran (10 mls) at -75° under nitrogen. The solution was kept at -75° for 1 hour, and then acetaldehyde (0.68 mls) was added dropwise and the mixture allowed to warm up. 2M Hydrochloric acid (20 mls) was added, the mixture was extracted with ether, the organic solution was dried (MgSO4) and the solvent was evaporated. The product was distilled to give the title compound as an oil (0.4 g). NMR (CDCl3) δ 7.17 (1H, d of t, 4-H), 6.75-6.6(2H, m, 3-H, 5-H), 5.24(1H, m, CHO--), 3.89(3H, s, OCH3), 3.27 (1H, d OH), 1.56(3H, d, CH3).

Workup

  1. temperatureto warm up
  2. extractionthe mixture was extracted with ether
  3. dry with materialthe organic solution was dried (MgSO4)
  4. customthe solvent was evaporated
  5. distillationThe product was distilled

Sources & evidence

ORD record
ord-45ea3f3c1b8741adaa7d1a989d659957
Source dataset
uspto-grants-1988_09
Patent number
US04769367

Reaction notes

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