Trifluoroacetic acid → HCID 23293654, compound

HRID 362823Notes

Reaction equation

HRID 362823 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2([CH2:19][C:20]([OH:22])=[O:21])O>ClCCl>[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12]/[C:13]/2=[CH:19]\[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23293567HCID 23293567, compound

Product 1

HCID 23293654HCID 23293654, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (25.1 mL) was added to a stirred, chilled (ice-methanol bath) solution of 2-(4-chloro-1-hydroxy-1-indanyl)acetic acid (10.4 g, 0.05 mol) in dichloromethane (230 mL). After 30 min, the mixture was concentrated in vacuo. Dichloromethane was added to the residue and the mixture was concentrated in vacuo to give 6.5 g (68%) of a white solid. Recrystallization of 0.98 g from acetonitrile: 2-propanol mixtures gave 0.62 g of a white solid: m.p., 233°-234° C.; NMR (DMSO-d6): d12.15 (br, 1H, COOH), 7.30-7.81 (m, 3H, Ar), 6.41 (s, 1H, =CH), 3.00-3.06, 3.19-3.22 (2m's, 4H, 2×CH2), steady-state nOe; irradiation at 6.41 d, observed 19.7% nOe at 7.79.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionDichloromethane was added to the residue
  3. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a6939ad1dc434d9895b8417b13f42377
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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