HCID 86597206, compound → HCID 11449463, compound

HRID 1666751Notes

Reaction equation

HRID 1666751 reaction equation
[Cl:1][C:2]([Cl:22])=[CH:3][C:4]1([CH3:21])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:20])[C:8]([CH3:19])=[C:9]([O:15]COC)[C:10]=2[CH3:14])[O:5]1>CO.Cl>[Cl:22][C:2]([Cl:1])=[CH:3][C:4]1([CH3:21])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:20])[C:8]([CH3:19])=[C:9]([OH:15])[C:10]=2[CH3:14])[O:5]1

Participants

4

Reactant 1

HCID 86597206HCID 86597206, compound

Product 1

HCID 11449463HCID 11449463, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution 160 mg of 2-(2,2-dichloro-vinyl)-6-methoxymethoxy-2,5,7,8-tetramethyl-chroman in 5 ml of methanol and 0.1 ml of conc. HCl was stirred overnight. The methanol was removed and the residue was mixed with ethyl acetate and water. Regular work-up and flash column chromatography on silica gel (15% ethyl acetate in hexane) afforded 70 mg of 2-(2,2-Dichloro-vinyl)-2,5,7,8-tetramethyl-chroman-6-ol. NMR (1H, CDCl3): 6.01 (1H, s), 4.26 (1H, s), 2.63 (2H, m), 2.48 (1H, m), 2.19 (3H, s), 2.16 (3H, s), 2.13 (3H, s), 1.78 (1H, m), 1.62 (3H, s). LC-MS: 301 (M+H, 100%), 323 (M+Na, 78%)

Workup

  1. customThe methanol was removed
  2. additionthe residue was mixed with ethyl acetate and water

Sources & evidence

ORD record
ord-b24257940ccc4639be6d41217a0b71e3
Source dataset
uspto-grants-2011_10
Patent number
US08044097B2

Reaction notes

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