Hydrochloric Acid → 3-[4-(6-Acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionic acid

HRID 1589700Notes

Reaction equation

HRID 1589700 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([Cl:33])[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O1CCCC1>[C:1]([O:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH:27]([Cl:33])[C:28]([OH:30])=[O:29])=[CH:24][CH:25]=1)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13605832HCID 13605832, compound

Product 1

HCID 134888703-[4-(6-Acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.16 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate was dissolved in a mixture of 1.5 ml of 99.5% ethanol and 0.2 ml of tetrahydrofuran. 265 mg of a 9.55% w/w aqueous solution of sodium hydroxide were added dropwise, under a nitrogen stream at 0°-4° C., to the resulting mixture. The mixture was then reacted for a further 20 hours at 0°-5° C., after which it was neutralized, whilst ice-cooling, by adding 0.68 g of a 10% w/w aqueous solution of hydrochloric acid. The solvent was then distilled off under reduced pressure. The separated light reddish oil was further extracted with chloroform, and the chloroform extract was washed with water and dried over anhydrous sodium sulfate. The crude product obtained by distilling off the chloroform under reduced pressure was subjected to column chromatography through silica gel and the desired 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionic acid was obtained from the fractions eluted with a 20:1 by volume mixture of benzene and 99.5% ethanol. Rf value on thin layer chromatography: 0.6 (tailing) [silica gel; developing solvent; benzene:99.5% ethanol=4:1 by volume].

Workup

  1. customThe mixture was then reacted for a further 20 hours at 0°-5° C.
  2. temperaturecooling
  3. distillationThe solvent was then distilled off under reduced pressure
  4. extractionThe separated light reddish oil was further extracted with chloroform
  5. extractionthe chloroform extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe crude product obtained
  9. distillationby distilling off the chloroform under reduced pressure

Sources & evidence

ORD record
ord-53a40f96d925483782c2b368d8433414
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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