HCID 69632012, compound → HCID 53826150, compound

HRID 1358780Notes

Reaction equation

HRID 1358780 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][OH:22])[CH:17]=2)[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:21]=[O:22])[CH:17]=2)[CH:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69632012HCID 69632012, compound

Product 1

HCID 53826150HCID 53826150, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolved 1.2 g (4 mmol) of 6-Hydroxymethyl-2-naphthalenecarboxylic acid benzyl ester in 100 ml of CH2Cl2, slowly added 5.2 g of MnO2 (60 mmol) and stirred at room temperature for 2 hours, then filtered through Ceilite. The Celite was washed with CH2Cl2 and combined organics taken to dryness. The oily residue was solidified with EtOAc/Hexanes (1:1) and collected by vacuum filtration, washed with small amount of methanol, dried to get 1.2 g of 6-Formyl-2-naphthalenecarboxylic acid benzyl ester. 1H NMR (400 MHz, DMSO-d6): δ 10.192 (s, 1H, —CHO), 8.754 (s, 1H, Ar—H), 8.667 (s, 1H, Ar—H), 8.327(t, J=9.4, 2H, Ar—H), 8.142(dd, J=1.6&7.0 Hz, 1H, Ar—H), 7.987-7.962 (dd, J=1.6&7.0 Hz, 1H, Ar—H), 7.544-7.526 (m, 2H, Ar—H), 7454-7.375 (m, 3H, Ar—H), 5.442 (s, 2H, —COOCH2—), MS m/e 289[M+−1].

Workup

  1. filtrationfiltered through Ceilite
  2. washThe Celite was washed with CH2Cl2
  3. filtrationcollected by vacuum filtration
  4. washwashed with small amount of methanol
  5. customdried

Sources & evidence

ORD record
ord-8b797fb3640242009e40c760a234fbb7
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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