Thionyl Chloride → HCID 21962640, compound

HRID 2211933Notes

Reaction equation

HRID 2211933 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, compoundYield 80%

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) is added. The reaction is refluxed for 5 hours and another batch of thionyl chloride (45 mL, 617 mmol) is added. The reaction is stirred overnight at room temperature. The solution is concentrated to a syrup and passed through a pad of silica gel (50 g), washed with 3% 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). NMR 1.26 (s, 6H), 1.28 (s, 6H), 1.68 (s, 4H), 2.25 (s, 3H), 4.00 (s, 2H), 6.11 (d, 1H), 7.10 (s, 1H), 7.11 (s, 1H), 7.41 (d, 1H).

Workup

  1. additionis added
  2. temperatureThe reaction is refluxed for 5 hours
  3. concentrationThe solution is concentrated to a syrup
  4. washwashed with 3% hexanes
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b271ac4ed8cc43939bf70b5e5ee87877
Source dataset
uspto-grants-2006_09
Patent number
US07101878B1

Reaction notes

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