Hydrochloric Acid → HCID 14210608, compound

HRID 580369Notes

Reaction equation

HRID 580369 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]([CH3:18])[C:8]2[O:13][C:12]([CH3:15])(O)[CH2:11][CH2:10][C:9]=2[C:16]=1[CH3:17])(=[O:3])[CH3:2].[ClH:20]>CCOCC>[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]([CH3:18])[C:8]2[O:13][C:12]([Cl:20])([CH3:15])[CH2:11][CH2:10][C:9]=2[C:16]=1[CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Product 1

HCID 14210608HCID 14210608, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g (37.9 mmol) of rac-3,4-dihydro-6-acetyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ol and 10 g of 4A molecular sieves in 200 mL of anhydrous ether was stirred with ice-bath cooling while HCl gas was bubbled in for 30 min. The mixture was filtered and the filtrate concentrated in vacuo. The residue was taken up in 600 mL of hexane and anhydrous CaCl2 was added. The mixture was stirred for 1 hr then filtered and the filtrate was concentrate in vacuo giving 4.3 g (40.2% yield) of rac-2-chloro-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol acetate as a colorless solid, mp 102°-106° C., which was unstable to column or thin layer chromatography.

Workup

  1. customwas bubbled in for 30 min
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. additionanhydrous CaCl2 was added
  5. stirringThe mixture was stirred for 1 hr
  6. filtrationthen filtered
  7. concentrationthe filtrate was concentrate in vacuo

Sources & evidence

ORD record
ord-a7b11dc1a5804385881c318aae96dad6
Source dataset
uspto-grants-1988_06
Patent number
US04752646

Reaction notes

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