Thionyl Chloride → HCID 21962640, compound

HRID 1070882Notes

Reaction equation

HRID 1070882 reaction equation
[CH3:1][C:2]1[C:3]([CH2:16][C:17]2[O:21][C:20]([C:22]([OH:24])=O)=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.S(Cl)([Cl:27])=O>C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:16][C:17]2[O:21][C:20]([C:22]([Cl:27])=[O:24])=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 21962625HCID 21962625, compound

Product 1

HCID 21962640HCID 21962640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid, 7, (20.15 g, 61.77 mmol) in methylene chloride (310 mL), thionyl chloride (45 mL, 617 mmol) was added. The reaction was heated under reflux for 5 hours and another batch of thionyl chloride (45 mL, 617 mmol) was added. The reaction was stirred overnight at room temperature. The solution was concentrated to a syrup and filtered through a pad of silica gel (50 g), eluted with 3% ethyl acetate in hexanes, and concentrated in vacuo to afford 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoyl chloride, 8 (17 g, 80% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe solution was concentrated to a syrup
  4. filtrationfiltered through a pad of silica gel (50 g)
  5. washeluted with 3% ethyl acetate in hexanes
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4788e943192a47c5a19db62a6241a955
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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